Tetrazolinones

ABSTRACT

Novel herbicidal tetrazolinone derivatives of the formula ##STR1## and intermediates therefor of the formula ##STR2## wherein R 1  is alkyl substituted by halogen, and 
     R 2  and R 3  each independently is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or substituted phenyl, or 
     R 2  and R 3  together with the N-atom to which they are attached, which may form a 5- or 6-membered heterocyclic ring.

TETRAZOLINONES

The present invention relates to tetrazolinone derivatives substituted by haloalkyl group, to a process for their preparation, to their use as herbicides, as well as to novel intermediates for their preparation and to processes for their preparation.

It is known that a group of certain 1-alkyltetrazolinone derivatives have herbicidal activities See: U.S. Pat. Nos. 4,618,365 (=EP 146279-A), 4,826,529, 4,830,661, 4,956,469, 5,003,075, 5,019,152, 5,120,346, 5,342,954, 5,344,814, 5,347,009, 5,347,010 and 5,362,704!.

There have now been found novel tetrazolinone derivatives represented by the following formula: ##STR3## wherein, R¹ is alkyl substituted by halogen, and

R² and R³ each independently is alkyl, alkenyl, alkynyl, cycloalkyl which may optionally be substituted, phenyl or substituted phenyl, or

R² and R³ together with the N-atom to which they are attached, are a 5- or 6-membered heterocyclic ring which may be substituted.

The tetrazolinone derivatives of the formula (I) are obtained

when

(a) compounds of the formula ##STR4## wherein R¹ has the same definition as above, are reacted with compounds represented by the formula: ##STR5## wherein R² and R³ have the same definitions as above and hal is chlorine or bromine,

in the presence of acid binders,

if appropriate in the presence of catalysts, and

if appropriate in the presence of inert solvents.

The tetrazolinone derivatives of formula (I) have strong herbicidal activities and are useful as herbicides.

Surprisingly the tetrazolinone derivatives of above formula (I) exhibit superior herbicidal activity to compounds known from the above-mentioned U.S. Pat. Nos. 4,618,365 (=European Pat. Application No. 146279-A), 4,826,529, 4,830,661, 4,956,469, 5,003,075, 5,019,152 and 5,120,346.

In this specification, the "alkyl substituted by halogen" comprises alkyl groups preferably having 1 to 6 carbon atoms in straight chain or branched chain substituted by 1 or more of fluorine, chlorine, bromine or iodine and, in the cases where a plural number of halogens exist, the halogen atoms may be either the same or different. Such halogen-substituted alkyl groups are exemplified by chloromethyl, bromomethyl, fluoromethyl, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, chloro-difluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoro-ethyl, 2-chloroethyl, 2-bromoethyl, 2-fluoroethyl, 1,1-dichloroethyl, 1,2-dichloroethyl, 2,2-dichloroethyl, 1,1-difluoroethyl, 1,2-difluoroethyl, 2,2-difluoroethyl, 2,2-dibromoethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, 2,3-dichloro-1,1,2,3,3-penta-fluoropropyl, 3-chloropropyl, 3-fluoropropyl, 3-bromo-propyl, 2,2,3,3,3-pentafluoropropyl, perfluoropropyl, and the like.

The "alkyl" comprises alkyl groups in straight chain or branched chain preferably having 1 to 8 carbon atoms and is exemplified by methyl, ethyl, propyl, isopropyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neo-pentyl, n-, iso-, sec-, tert- or neo-hexyl, heptyl, octyl, and the like.

The "alkenyl" comprises alkenyl groups in straight chain or branched chain preferably having 2 to 8 carbon atoms and is exemplified by vinyl, allyl, isopropenyl, 1-methyl-2-propenyl, 2- or 3-butenyl, 2-, 3- or 4-pentenyl, and the like.

The "alkynyl" comprises alkynyl groups in straight chain or branched chain preferably having 3 to 8 carbon atoms and is exemplified by propargyl, 1-methyl-2-propynyl, 2- or 3-butynyl, 2-, 3- or 4-pentynyl, and the like.

The "cycloalkyl" comprises alkyl groups in cyclic ring form having preferably 3 to 8 of carbon atoms and is exemplified by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like, and such cycloalkyls may optionally be substituted. The substituent may be, for example, alkyl (such as methyl, ethyl, propyl, isopropyl, n-, iso-, sec- or tert-butyl or the like).

The substituted phenyl comprises phenyls having at least one substituent on the ring and, in cases where a plural number of substituents exist, such substituents may be either the same or different. The possible substituents comprise, for example, halogen (comprising fluorine, chlorine, bromine and iodine preferably fluorine, chlorine or bromine), cyano, nitro, alkyl (such as methyl, ethyl, propyl, isopropyl, n-, iso-, sec- or tert-butyl, and the like), haloalkyl (methyl, ethyl, propyl, isopropyl, n-, iso-, sec- or tert-butyl, and the like respectively substituted by at least one of fluorine, chlorine, bromine and iodine), alkoxy (such as methoxy, ethoxy, propoxy, isopropoxy, n-, iso-, sec- or tert-butoxy, and the like), haloalkoxy (such as methoxy, ethoxy, propoxy, isopropoxy, n-, iso-, sec- or tert-butoxy, and the like, respectively substituted by at least one of fluorine, chlorine, bromine and iodine), alkylthio (such as methylthio, ethylthio, propylthio, isopropylthio and n-, iso-, sec- or tert-butylthio), haloalkylthio (such as methylthio, ethylthio, propylthio, isopropylthio, n-, iso-, sec- or tert-butylthio, respectively substituted by at least one of fluorine, chlorine, bromine and iodine), and others.

The 5- or 6-membered heterocyclic ring comprises heterocyclic rings which contain at least one nitrogen atom as the heteroatom and may optionally contain a further heteroatom selected from the group consisting of nitrogen, oxygen and sulfur. Such heterocyclic rings may optionally be substituted by alkyl and further may be optionally condensed with a cyclic hydrocarbon group. Examples thereof include pyrrolidino, pyrrolyl, imidazolidinyl, piperidino, morpholino, pyrazolyl, indol-1-yl, perhydroindol-1-yl, 1,2,3,4-tetrahydroquinolin-1-yl, 2-methyl-1,1,2,2-tetra-hydroquinolin-1-yl, perhydroquinolin-1-yl, and the like.

Among the tetrazolinone derivatives according to the invention, of the formula (I), preferred compounds are those

in which

R¹ is C₁₋₆ alkyl which is substituted by one or more of fluorine, chlorine or bromine, and

R² and R³ each independently is C₁₋₆ alkyl, C₂₋₆ alkenyl, C₃₋₆ alkynyl, C₃₋₈ cycloalkyl which may optionally be substituted by C₁₋₆ alkyl, phenyl, or phenyl having at least one substituent selected from the group consisting of halogen, cyano, nitro, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio and C₁₋₄ haloalkylthio, or

R² and R³ together with the N-atom to which they are attached, are a 5- or 6-membered saturated heterocyclic ring, optionally substituted by alkyl and/or condensed with a cyclic hydrocarbon.

Very particularly preferred tetrazolinone derivatives of the formula (I) are those

in which

R¹ is C₁₋₃ alkyl which is substituted by one or more of fluorine, chlorine or bromine, and

R² and R³ each independently is C₁₋₄ alkyl, cyclopropyl which may optionally be substituted by methyl, cyclopentyl which may optionally be substituted by methyl, cyclohexyl which may optionally be substituted by methyl, allyl, propargyl, phenyl, or phenyl having at least one substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, methylthio, nitro, cyano, trifluoromethyl, trifluoro-methoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, trifluoromethylthio and 2,2,2-trifluoro-ethylthio, or

R² and R³ together with the N-atom to which they are attached, are piperidino, methylpiperidino, morpholino, indol-1-yl, perhydroindol-1-yl, 1,2,3,4-tetrahydro-quinolin-1-yl, 2-methyl-1,2,3,4-tetrahydroquinolin-1-yl or perhydroquinolin-1-yl.

Specific tetrazolinone derivatives of formula (I) are shown in the following Table 1 and Table 2. Table 1 illustrates tetrazolinone derivatives of formula (I) in which R¹ and R² are groups which are independent of each other and Table 2 illustrates tetrazolinone derivatives of formula (I) in which R¹ and R² are a heterocyclic ring together with the N-atom to which they are attached.

                  TABLE 1                                                          ______________________________________                                          ##STR6##                                                                      R.sup.1   R.sup.2   R.sup.3                                                    ______________________________________                                         ClCH.sub.2                                                                               ethyl     ethyl                                                      ClCH.sub.2                                                                               ethyl     cyclohexyl                                                 ClCH.sub.2                                                                               n-propyl  n-propyl                                                   ClCH.sub.2                                                                               n-propyl  cyclopropyl                                                ClCH.sub.2                                                                               n-propyl  cyclopentyl                                                ClCH.sub.2                                                                               allyl     allyl                                                      ClCH.sub.2                                                                               propargyl propargyl                                                  ClCH.sub.2                                                                               isopropyl phenyl                                                     ClCH.sub.2                                                                               isopropyl 2-fluorophenyl                                             ClCH.sub.2                                                                               isopropyl 3-fluorophenyl                                             ClCH.sub.2                                                                               isopropyl 4-fluorophenyl                                             ClCH.sub.2                                                                               isopropyl 2-chlorophenyl                                             ClCH.sub.2                                                                               isopropyl 3-chlorophenyl                                             ClCH.sub.2                                                                               isopropyl 4-chlorophenyl                                             ClCH.sub.2                                                                               isopropyl 2,3-dichlorophenyl                                         ClCH.sub.2                                                                               isopropyl 2,4-dichlorophenyl                                         ClCH.sub.2                                                                               isopropyl 2,5-dichlorophenyl                                         ClCH.sub.2                                                                               isopropyl 2,6-dichlorophenyl                                         ClCH.sub.2                                                                               isopropyl 3,4-dichlorophenyl                                         ClCH.sub.2                                                                               isopropyl 3,5-dichlorophenyl                                         ClCH.sub.2                                                                               isopropyl 2,4,6-trichlorophenyl                                      ClCH.sub.2                                                                               isopropyl 2-chloro-3-methylphenyl                                    ClCH.sub.2                                                                               isopropyl 2-chloro-4-methylphenyl                                    ClCH.sub.2                                                                               isopropyl 2-chloro-5-methylphenyl                                    ClCH.sub.2                                                                               isopropyl 2-chloro-6-methylphenyl                                    ClCH.sub.2                                                                               isopropyl 3-chloro-4-methylphenyl                                    ClCH.sub.2                                                                               isopropyl 3-chloro-4-trifluoromethylphenyl                           ClCH.sub.2                                                                               isopropyl 3-chloro-4-trifluromethoxyphenyl                           ClCH.sub.2                                                                               isopropyl 3-chloro-4-trifluoromethylthiophenyl                       ClCH.sub.2                                                                               isopropyl 2-bromophenyl                                              ClCH.sub.2                                                                               isopropyl 2-trifluoromethylphenyl                                    ClCH.sub.2                                                                               isopropyl 3-trifluoromethylphenyl                                    ClCH.sub.2                                                                               isopropyl 4-trifluoromethylphenyl                                    ClCH.sub.2                                                                               isopropyl 2-trifluromethoxyphenyl                                    ClCH.sub.2                                                                               isopropyl 2-difluoromethoxyphenyl                                    ClCH.sub.2                                                                               isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            ClCH.sub.2                                                                               isopropyl 2 trifluoromethylthiophenyl                                ClCH.sub.2                                                                               isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         ClCH.sub.2                                                                               isopropyl 2-methylphenyl                                             ClCH.sub.2                                                                               isopropyl 3-methylphenyl                                             ClCH.sub.2                                                                               isopropyl 4-methylphenyl                                             ClCH.sub.2                                                                               isopropyl 2,3-dimethylphenyl                                         ClCH.sub.2                                                                               isopropyl 2,4-dimethylphenyl                                         ClCH.sub.2                                                                               isopropyl 2,5-dimethylphenyl                                         ClCH.sub.2                                                                               isopropyl 2,6-dimethylphenyl                                         ClCH.sub.2                                                                               isopropyl 2,4,6-trimethylphenyl                                      ClCH.sub.2                                                                               isopropyl 2-ethylphenyl                                              ClCH.sub.2                                                                               isopropyl 3-ethylphenyl                                              ClCH.sub.2                                                                               isopropyl 4-ethylphenyl                                              ClCH.sub.2                                                                               isopropyl 2-methoxyphenyl                                            ClCH.sub.2                                                                               isopropyl 3-methoxyphenyl                                            ClCH.sub.2                                                                               isopropyl 4-methoxyphenyl                                            ClCH.sub.2                                                                               isopropyl 2-methylthiophenyl                                         ClCH.sub.2                                                                               isopropyl 2-nitrophenyl                                              ClCH.sub.2                                                                               isopropyl 2-cyanophenyl                                              BrCH.sub.2                                                                               ethyl     ethyl                                                      BrCH.sub.2                                                                               ethyl     cyclohexyl                                                 BrCH.sub.2                                                                               n-propyl  n-propyl                                                   BrCH.sub.2                                                                               n-propyl  cyclopropyl                                                BrCH.sub.2                                                                               n-propyl  cyclopentyl                                                BrCH.sub.2                                                                               allyl     allyl                                                      BrCH.sub.2                                                                               propargyl propargyl                                                  BrCH.sub.2                                                                               methyl    phenyl                                                     BrCH.sub.2                                                                               ethyl     phenyl                                                     BrCH.sub.2                                                                               n-propyl  phenyl                                                     BrCH.sub.2                                                                               isopropyl phenyl                                                     BrCH.sub.2                                                                               n-butyl   phenyl                                                     BrCH.sub.2                                                                               s-butyl   phenyl                                                     BrCH.sub.2                                                                               isobutyl  phenyl                                                     BrCH.sub.2                                                                               phenyl    phenyl                                                     BrCH.sub.2                                                                               isopropyl 2-fluorophenyl                                             BrCH.sub.2                                                                               isopropyl 3-fluorophenyl                                             BrCH.sub.2                                                                               isopropyl 4-fluorophenyl                                             BrCH.sub.2                                                                               isopropyl 2-chlorophenyl                                             BrCH.sub.2                                                                               isopropyl 3-chlorophenyl                                             BrCH.sub.2                                                                               isopropyl 4-chlorophenyl                                             BrCH.sub.2                                                                               isopropyl 2,3-dichlorophenyl                                         BrCH.sub.2                                                                               isopropyl 2,4-dichlorophenyl                                         BrCH.sub.2                                                                               isopropyl 2,5-dichlorophenyl                                         BrCH.sub.2                                                                               isopropyl 2,6-dichlorophenyl                                         BrCH.sub.2                                                                               isopropyl 3,4-dichlorophenyl                                         BrCH.sub.2                                                                               isopropyl 3,5-dichlorophenyl                                         BrCH.sub.2                                                                               isopropyl 2,4,6-trichlorophenyl                                      BrCH.sub.2                                                                               isopropyl 2-chloro-3-methylphenyl                                    BrCH.sub.2                                                                               isopropyl 2-chloro-4-methylphenyl                                    BrCH.sub.2                                                                               isopropyl 2-chloro-5-methylphenyl                                    BrCH.sub.2                                                                               isopropyl 2-chloro-6-methylphenyl                                    BrCH.sub.2                                                                               isopropyl 3-chloro-4-methylphenyl                                    BrCH.sub.2                                                                               isopropyl 3-chloro-4-trifluoromethylphenyl                           BrCH.sub.2                                                                               isopropyl 3-chloro-4-trifluromethoxyphenyl                           BrCH.sub.2                                                                               isopropyl 3-chloro-4-trifluoromethylthiophenyl                       BrCH.sub.2                                                                               isopropyl 2-bromophenyl                                              BrCH.sub.2                                                                               isopropyl 2-trifluoromethylphenyl                                    BrCH.sub.2                                                                               isopropyl 3-trifluoromethylphenyl                                    BrCH.sub.2                                                                               isopropyl 4-trifluoromethylphenyl                                    BrCH.sub.2                                                                               isopropyl 2-trifluromethoxyphenyl                                    BrCH.sub.2                                                                               isopropyl 2-difluoromethoxyphenyl                                    BrCH.sub.2                                                                               isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            BrCH.sub.2                                                                               isopropyl 2-trifluoromethylthiophenyl                                BrCH.sub.2                                                                               isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         BrCH.sub.2                                                                               isopropyl 2-methylphenyl                                             BrCH.sub.2                                                                               isopropyl 3-methylphenyl                                             BrCH.sub.2                                                                               isopropyl 4-methylphenyl                                             BrCH.sub.2                                                                               isopropyl 2,3-dimethylphenyl                                         BrCH.sub.2                                                                               isopropyl 2,4-dimethylphenyl                                         BrCH.sub.2                                                                               isopropyl 2,5-dimethylphenyl                                         BrCH.sub.2                                                                               isopropyl 2,6-dimethylphenyl                                         BrCH.sub.2                                                                               isopropyl 2,4,6-trimethylphenyl                                      BrCH.sub.2                                                                               isopropyl 2-ethylphenyl                                              BrCH.sub.2                                                                               isopropyl 3-ethylphenyl                                              BrCH.sub.2                                                                               isopropyl 4-ethylphenyl                                              BrCH.sub.2                                                                               isopropyl 2-methoxyphenyl                                            BrCH.sub.2                                                                               isopropyl 3-methoxyphenyl                                            BrCH.sub.2                                                                               isopropyl 4-methoxyphenyl                                            BrCH.sub.2                                                                               isopropyl 2-methylthiophenyl                                         BrCH.sub.2                                                                               isopropyl 2-nitrophenyl                                              BrCH.sub.2                                                                               isopropyl 2-cyanophenyl                                              FCH.sub.2 ethyl     ethyl                                                      FCH.sub.2 ethyl     cyclohexyl                                                 FCH.sub.2 n-propyl  n-propyl                                                   FCH.sub.2 n-propyl  cyclopropyl                                                FCH.sub.2 n-propyl  cyclopentyl                                                FCH.sub.2 allyl     allyl                                                      FCH.sub.2 propargyl propargyl                                                  FCH.sub.2 methyl    phenyl                                                     FCH.sub.2 ethyl     phenyl                                                     FCH.sub.2 n-propyl  phenyl                                                     FCH.sub.2 isopropyl phenyl                                                     FCH.sub.2 n-butyl   phenyl                                                     FCH.sub.2 s-butyl   phenyl                                                     FCH.sub.2 isobutyl  phenyl                                                     FCH.sub.2 phenyl    phenyl                                                     FCH.sub.2 isopropyl 2-fluorophenyl                                             FCH.sub.2 isopropyl 3-fluorophenyl                                             FCH.sub.2 isopropyl 4-fluorophenyl                                             FCH.sub.2 isopropyl 2-chlorophenyl                                             FCH.sub.2 isopropyl 3-chlorophenyl                                             FCH.sub.2 isopropyl 4-chlorophenyl                                             FCH.sub.2 isopropyl 2,3-dichlorophenyl                                         FCH.sub.2 isopropyl 2,4-dichlorophenyl                                         FCH.sub.2 isopropyl 2,5-dichlorophenyl                                         FCH.sub.2 isopropyl 2,6-dichlorophenyl                                         FCH.sub.2 isopropyl 3,4-dichlorophenyl                                         FCH.sub.2 isopropyl 3,5-dichlorophenyl                                         FCH.sub.2 isopropyl 2,4,6-trichlorophenyl                                      FCH.sub.2 isopropyl 2-chloro-3-methylphenyl                                    FCH.sub.2 isopropyl 2-chloro-4-methylphenyl                                    FCH.sub.2 isopropyl 2-chloro-5-methylphenyl                                    FCH.sub.2 isopropyl 2-chloro-6-methylphenyl                                    FCH.sub.2 isopropyl 3-chloro-4-methylphenyl                                    FCH.sub.2 isopropyl 3-chloro-4-trifluoromethylphenyl                           FCH.sub.2 isopropyl 3-chloro-4-trifluromethoxyphenyl                           FCH.sub.2 isopropyl 3-chloro-4-trifluoromethylthiophenyl                       FCH.sub.2 isopropyl 2-bromophenyl                                              FCH.sub.2 isopropyl 2-trifluoromethylphenyl                                    FCH.sub.2 isopropyl 3-trifluoromethylphenyl                                    FCH.sub.2 isopropyl 4-trifluoromethylphenyl                                    FCH.sub.2 isopropyl 2-trifluromethoxyphenyl                                    FCH.sub.2 isopropyl 2-difluoromethoxyphenyl                                    FCH.sub.2 isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            FCH.sub.2 isopropyl 2-trifluoromethylthiophenyl                                FCH.sub.2 isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         FCH.sub.2 isopropyl 2-methylphenyl                                             FCH.sub.2 isopropyl 3-methylphenyl                                             FCH.sub.2 isopropyl 4-methylphenyl                                             FCH.sub.2 isopropyl 2,3-dimethylphenyl                                         FCH.sub.2 isopropyl 2,4-dimethylphenyl                                         FCH.sub.2 isopropyl 2,5-dimethylphenyl                                         FCH.sub.2 isopropyl 2,6-dimethylphenyl                                         FCH.sub.2 isopropyl 2,4,6-trimethylphenyl                                      FCH.sub.2 isopropyl 2-ethylphenyl                                              FCH.sub.2 isopropyl 3-ethylphenyl                                              FCH.sub.2 isopropyl 4-ethylphenyl                                              FCH.sub.2 isopropyl 2-methoxyphenyl                                            FCH.sub.2 isopropyl 3-methoxyphenyl                                            FCH.sub.2 isopropyl 4-methoxyphenyl                                            FCH.sub.2 isopropyl 2-methylthiophenyl                                         FCH.sub.2 isopropyl 2-nitrophenyl                                              FCH.sub.2 isopropyl 2-cyanophenyl                                              Cl.sub.2 HC                                                                              ethyl     ethyl                                                      Cl.sub.2 HC                                                                              ethyl     cyclohexyl                                                 Cl.sub.2 HC                                                                              ethyl     2-methylcyclohexyl                                         Cl.sub.2 HC                                                                              n-propyl  n-propyl                                                   Cl.sub.2 HC                                                                              n-propyl  cyclopropyl                                                Cl.sub.2 HC                                                                              n-propyl  cyclopentyl                                                Cl.sub.2 HC                                                                              allyl     allyl                                                      Cl.sub.2 HC                                                                              propargyl propargyl                                                  Cl.sub.2 HC                                                                              methyl    phenyl                                                     Cl.sub.2 HC                                                                              ethyl     phenyl                                                     Cl.sub.2 HC                                                                              n-propyl  phenyl                                                     Cl.sub.2 HC                                                                              isopropyl phenyl                                                     Cl.sub.2 HC                                                                              n-butyl   phenyl                                                     Cl.sub.2 HC                                                                              s-butyl   phenyl                                                     Cl.sub.2 HC                                                                              isobutyl  phenyl                                                     Cl.sub.2 HC                                                                              phenyl    phenyl                                                     Cl.sub.2 HC                                                                              isopropyl 2-fluorophenyl                                             Cl.sub.2 HC                                                                              isopropyl 3-fluorophenyl                                             Cl.sub.2 HC                                                                              isopropyl 4-fluorophenyl                                             Cl.sub.2 HC                                                                              isopropyl 2-chlorophenyl                                             Cl.sub.2 HC                                                                              isopropyl 3-chlorophenyl                                             Cl.sub.2 HC                                                                              isopropyl 4-chlorophenyl                                             Cl.sub.2 HC                                                                              isopropyl 2,3-dichlorophenyl                                         Cl.sub.2 HC                                                                              isopropyl 2,4-dichlorophenyl                                         Cl.sub.2 HC                                                                              isopropyl 2,5-dichlorophenyl                                         Cl.sub.2 HC                                                                              isopropyl 2,6-dichlorophenyl                                         Cl.sub.2 HC                                                                              isopropyl 3,4-dichlorophenyl                                         Cl.sub.2 HC                                                                              isopropyl 3,5-dichlorophenyl                                         Cl.sub.2 HC                                                                              isopropyl 2,4,6-trichlorophenyl                                      Cl.sub.2 HC                                                                              isopropyl 2-chloro-3-methylphenyl                                    Cl.sub.2 HC                                                                              isopropyl 2-chloro-4-methylphenyl                                    Cl.sub.2 HC                                                                              isopropyl 2-chloro-5-methylphenyl                                    Cl.sub.2 HC                                                                              isopropyl 2-chloro-6-methylphenyl                                    Cl.sub.2 HC                                                                              isopropyl 3-chloro-4-methylphenyl                                    Cl.sub.2 HC                                                                              isopropyl 3-chloro-4-trifluoromethylphenyl                           Cl.sub.2 HC                                                                              isopropyl 3-chloro-4-trifluromethoxyphenyl                           Cl.sub.2 HC                                                                              isopropyl 3-chloro-4-trifluoromethylthiophenyl                       Cl.sub.2 HC                                                                              isopropyl 2-bromophenyl                                              Cl.sub.2 HC                                                                              isopropyl 2-trifluoromethylphenyl                                    Cl.sub.2 HC                                                                              isopropyl 3-trifluoromethylphenyl                                    Cl.sub.2 HC                                                                              isopropyl 4-trifluoromethylphenyl                                    Cl.sub.2 HC                                                                              isopropyl 2-trifluromethoxyphenyl                                    Cl.sub.2 HC                                                                              isopropyl 2-difluoromethoxyphenyl                                    Cl.sub.2 HC                                                                              isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            Cl.sub.2 HC                                                                              isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         Cl.sub.2 HC                                                                              isopropyl 2-trifluoromethylthiophenyl                                Cl.sub.2 HC                                                                              isopropyl 2-methylphenyl                                             Cl.sub.2 HC                                                                              isopropyl 3-methylphenyl                                             Cl.sub.2 HC                                                                              isopropyl 4-methylphenyl                                             Cl.sub.2 HC                                                                              isopropyl 2,3-dimethylphenyl                                         Cl.sub.2 HC                                                                              isopropyl 2,4-dimethylphenyl                                         Cl.sub.2 HC                                                                              isopropyl 2,5-dimethylphenyl                                         Cl.sub.2 HC                                                                              isopropyl 2,6-dimethylphenyl                                         Cl.sub.2 HC                                                                              isopropyl 2,4,6-trimethylphenyl                                      Cl.sub.2 HC                                                                              isopropyl 2-ethylphenyl                                              Cl.sub.2 HC                                                                              isopropyl 3-ethylphenyl                                              Cl.sub.2 HC                                                                              isopropyl 4-ethylphenyl                                              Cl.sub.2 HC                                                                              isopropyl 2-methoxyphenyl                                            Cl.sub.2 HC                                                                              isopropyl 3-methoxyphenyl                                            Cl.sub.2 HC                                                                              isopropyl 4-methoxyphenyl                                            Cl.sub.2 HC                                                                              isopropyl 2-methylthiophenyl                                         Cl.sub.2 HC                                                                              isopropyl 2-nitrophenyl                                              Cl.sub.2 HC                                                                              isopropyl 2-cyanophenyl                                              F.sub.2 HC                                                                               ethyl     ethyl                                                      F.sub.2 HC                                                                               ethyl     cyclohexyl                                                 F.sub.2 HC                                                                               n-propyl  n-propyl                                                   F.sub.2 HC                                                                               n-propyl  cyclopropyl                                                F.sub.2 HC                                                                               n-propyl  cyclopentyl                                                F.sub.2 HC                                                                               allyl     allyl                                                      F.sub.2 HC                                                                               propargyl propargyl                                                  F.sub.2 HC                                                                               methyl    phenyl                                                     F.sub.2 HC                                                                               ethyl     phenyl                                                     F.sub.2 HC                                                                               n-propyl  phenyl                                                     F.sub.2 HC                                                                               isopropyl phenyl                                                     F.sub.2 HC                                                                               n-butyl   phenyl                                                     F.sub.2 HC                                                                               s-butyl   phenyl                                                     F.sub.2 HC                                                                               isobutyl  phenyl                                                     F.sub.2 HC                                                                               phenyl    phenyl                                                     F.sub.2 HC                                                                               isopropyl 2-fluorophenyl                                             F.sub.2 HC                                                                               isopropyl 3-fluorophenyl                                             F.sub.2 HC                                                                               isopropyl 4-fluorophenyl                                             F.sub.2 HC                                                                               isopropyl 2-chlorophenyl                                             F.sub.2 HC                                                                               isopropyl 3-chlorophenyl                                             F.sub.2 HC                                                                               isopropyl 4-chlorophenyl                                             F.sub.2 HC                                                                               isopropyl 2,3-dichlorophenyl                                         F.sub.2 HC                                                                               isopropyl 2,4-dichlorophenyl                                         F.sub.2 HC                                                                               isopropyl 2,5-dichlorophenyl                                         F.sub.2 HC                                                                               isopropyl 2,6-dichlorophenyl                                         F.sub.2 HC                                                                               isopropyl 3,4-dichlorophenyl                                         F.sub.2 HC                                                                               isopropyl 3,5-dichlorophenyl                                         F.sub.2 HC                                                                               isopropyl 2,4,6-trichlorophenyl                                      F.sub.2 HC                                                                               isopropyl 2-chloro-3-methylphenyl                                    F.sub.2 HC                                                                               isopropyl 2 chloro-4-methylphenyl                                    F.sub.2 HC                                                                               isopropyl 2-chloro-5-methylphenyl                                    F.sub.2 HC                                                                               isopropyl 2-chloro-6-methylphenyl                                    F.sub.2 HC                                                                               isopropyl 3-chloro-4-methylphenyl                                    F.sub.2 HC                                                                               isopropyl 3-chloro-4-trifluoromethylphenyl                           F.sub.2 HC                                                                               isopropyl 3-chloro-4-trifluromethoxyphenyl                           F.sub.2 HC                                                                               isopropyl 3-chloro-4-trifluoromethylthiophenyl                       F.sub.2 HC                                                                               isopropyl 2-bromophenyl                                              F.sub.2 HC                                                                               isopropyl 2-trifluoromethylphenyl                                    F.sub.2 HC                                                                               isopropyl 3-trifluoromethylphenyl                                    F.sub.2 HC                                                                               isopropyl 4-trifluoromethylphenyl                                    F.sub.2 HC                                                                               isopropyl 2-trifluromethoxyphenyl                                    F.sub.2 HC                                                                               isopropyl 2-difluoromethoxyphenyl                                    F.sub.2 HC                                                                               isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            F.sub.2 HC                                                                               isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         F.sub.2 HC                                                                               isopropyl 2-trifluoromethylthiophenyl                                F.sub.2 HC                                                                               isopropyl 2-methylphenyl                                             F.sub.2 HC                                                                               isopropyl 3-methylphenyl                                             F.sub.2 HC                                                                               isopropyl 4-methylphenyl                                             F.sub.2 HC                                                                               isopropyl 2,3-dimethylphenyl                                         F.sub.2 HC                                                                               isopropyl 2,4-dimethylphenyl                                         F.sub.2 HC                                                                               isopropyl 2,5-dimethylphenyl                                         F.sub.2 HC                                                                               isopropyl 2,6-dimethylphenyl                                         F.sub.2 HC                                                                               isopropyl 2,4,6-trimethylphenyl                                      F.sub.2 HC                                                                               isopropyl 2-ethylphenyl                                              F.sub.2 HC                                                                               isopropyl 3-ethylphenyl                                              F.sub.2 HC                                                                               isopropyl 4-ethylphenyl                                              F.sub.2 HC                                                                               isopropyl 2-methoxyphenyl                                            F.sub.2 HC                                                                               isopropyl 3-methoxyphenyl                                            F.sub.2 HC                                                                               isopropyl 4-methoxyphenyl                                            F.sub.2 HC                                                                               isopropyl 2-methylthiophenyl                                         F.sub.2 HC                                                                               isopropyl 2-nitrophenyl                                              F.sub.2 HC                                                                               isopropyl 2-cyanophenyl                                              Cl.sub.3 C                                                                               ethyl     ethyl                                                      Cl.sub.3 C                                                                               ethyl     cyclohexyl                                                 Cl.sub.3 C                                                                               n-propyl  n-propyl                                                   Cl.sub.3 C                                                                               n-propyl  cyclopropyl                                                Cl.sub.3 C                                                                               n-propyl  cyclopentyl                                                Cl.sub.3 C                                                                               allyl     allyl                                                      Cl.sub.3 C                                                                               propargyl propargyl                                                  Cl.sub.3 C                                                                               methyl    phenyl                                                     Cl.sub.3 C                                                                               ethyl     phenyl                                                     Cl.sub.3 C                                                                               n-propyl  phenyl                                                     Cl.sub.3 C                                                                               isopropyl phenyl                                                     Cl.sub.3 C                                                                               n-butyl   phenyl                                                     Cl.sub.3 C                                                                               s-butyl   phenyl                                                     Cl.sub.3 C                                                                               isobutyl  phenyl                                                     Cl.sub.3 C                                                                               phenyl    phenyl                                                     Cl.sub.3 C                                                                               isopropyl 2-fluorophenyl                                             Cl.sub.3 C                                                                               isopropyl 3-fluorophenyl                                             Cl.sub.3 C                                                                               isopropyl 4-fluorophenyl                                             Cl.sub.3 C                                                                               isopropyl 2-chlorophenyl                                             Cl.sub.3 C                                                                               isopropyl 3-chlorophenyl                                             Cl.sub.3 C                                                                               isopropyl 4-chlorophenyl                                             Cl.sub.3 C                                                                               isopropyl 2,3-dichlorophenyl                                         Cl.sub.3 C                                                                               isopropyl 2,4-dichlorophenyl                                         Cl.sub.3 C                                                                               isopropyl 2,5-dichlorophenyl                                         Cl.sub.3 C                                                                               isopropyl 2,6-dichlorophenyl                                         Cl.sub.3 C                                                                               isopropyl 3,4-dichlorophenyl                                         Cl.sub.3 C                                                                               isopropyl 3,5-dichlorophenyl                                         Cl.sub.3 C                                                                               isopropyl 2,4,6-trichlorophenyl                                      Cl.sub.3 C                                                                               isopropyl 2-chloro-3-methylphenyl                                    Cl.sub.3 C                                                                               isopropyl 2-chloro-4-methylphenyl                                    Cl.sub.3 C                                                                               isopropyl 2-chloro-5-methylphenyl                                    Cl.sub.3 C                                                                               isopropyl 2-chloro-6-methylphenyl                                    Cl.sub.3 C                                                                               isopropyl 3-chloro-4-methylphenyl                                    Cl.sub.3 C                                                                               isopropyl 3-chloro-4-trifluoromethylphenyl                           Cl.sub.3 C                                                                               isopropyl 3-chloro-4-trifluromethoxyphenyl                           Cl.sub.3 C                                                                               isopropyl 3-chloro-4-trifluoromethylthiophenyl                       Cl.sub.3 C                                                                               isopropyl 2-bromophenyl                                              Cl.sub.3 C                                                                               isopropyl 2-trifluoromethylphenyl                                    Cl.sub.3 C                                                                               isopropyl 3-trifluoromethylphenyl                                    Cl.sub.3 C                                                                               isopropyl 4-trifluoromethylphenyl                                    Cl.sub.3 C                                                                               isopropyl 2-trifluromethoxyphenyl                                    Cl.sub.3 C                                                                               isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            Cl.sub.3 C                                                                               isopropyl 2-difluoromethoxyphenyl                                    Cl.sub.3 C                                                                               isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         Cl.sub.3 C                                                                               isopropyl 2-trifluoromethylthiophenyl                                Cl.sub.3 C                                                                               isopropyl 2-methylphenyl                                             Cl.sub.3 C                                                                               isopropyl 3-methylphenyl                                             Cl.sub.3 C                                                                               isopropyl 4-methylphenyl                                             Cl.sub.3 C                                                                               isopropyl 2,3-dimethylphenyl                                         Cl.sub.3 C                                                                               isopropyl 2,4-dimethylphenyl                                         Cl.sub.3 C                                                                               isopropyl 2,5-dimethylphenyl                                         Cl.sub.3 C                                                                               isopropyl 2,6-dimethylphenyl                                         Cl.sub.3 C                                                                               isopropyl 2,4,6-trimethylphenyl                                      Cl.sub.3 C                                                                               isopropyl 2-ethylphenyl                                              Cl.sub.3 C                                                                               isopropyl 3-ethylphenyl                                              Cl.sub.3 C                                                                               isopropyl 4-ethylphenyl                                              Cl.sub.3 C                                                                               isopropyl 2-methoxyphenyl                                            Cl.sub.3 C                                                                               isopropyl 3-methoxyphenyl                                            Cl.sub.3 C                                                                               isopropyl 4-methoxyphenyl                                            Cl.sub.3 C                                                                               isopropyl 2-methylthiophenyl                                         Cl.sub.3 C                                                                               isopropyl 2-nitrophenyl                                              Cl.sub.3 C                                                                               isopropyl 2-cyanophenyl                                              F.sub.3 C ethyl     ethyl                                                      F.sub.3 C ethyl     cyclohexyl                                                 F.sub.3 C n-propyl  n-propyl                                                   F.sub.3 C n-propyl  cyclopropyl                                                F.sub.3 C n-propyl  cyclopentyl                                                F.sub.3 C allyl     allyl                                                      F.sub.3 C propargyl propargyl                                                  F.sub.3 C methyl    phenyl                                                     F.sub.3 C ethyl     phenyl                                                     F.sub.3 C n-propyl  phenyl                                                     F.sub.3 C isopropyl phenyl                                                     F.sub.3 C n-butyl   phenyl                                                     F.sub.3 C s-butyl   phenyl                                                     F.sub.3 C isobutyl  phenyl                                                     F.sub.3 C phenyl    phenyl                                                     F.sub.3 C isopropyl 2-fluorophenyl                                             F.sub.3 C isopropyl 3-fluorophenyl                                             F.sub.3 C isopropyl 4-fluorophenyl                                             F.sub.3 C isopropyl 2-chlorophenyl                                             F.sub.3 C isopropyl 3-chlorophenyl                                             F.sub.3 C isopropyl 4-chlorophenyl                                             F.sub.3 C isopropyl 2,3-dichlorophenyl                                         F.sub.3 C isopropyl 2,4-dichlorophenyl                                         F.sub.3 C isopropyl 2,5-dichlorophenyl                                         F.sub.3 C isopropyl 2,6-dichlorophenyl                                         F.sub.3 C isopropyl 3,4-dichlorophenyl                                         F.sub.3 C isopropyl 3,5-dichlorophenyl                                         F.sub.3 C isopropyl 2,4,6-trichlorophenyl                                      F.sub.3 C isopropyl 2-chloro-3-methylphenyl                                    F.sub.3 C isopropyl 2-chloro-4-methylphenyl                                    F.sub.3 C isopropyl 2-chloro-5-methylphenyl                                    F.sub.3 C isopropyl 2-chloro-6-methylphenyl                                    F.sub.3 C isopropyl 3-chloro-4-methylphenyl                                    F.sub.3 C isopropyl 3-chloro-4-trifluoromethylphenyl                           F.sub.3 C isopropyl 3-chloro-4-trifluromethoxyphenyl                           F.sub.3 C isopropyl 3-chloro-4-trifluoromethylthiophenyl                       F.sub.3 C isopropyl 2-bromophenyl                                              F.sub.3 C isopropyl 2-trifluoromethylphenyl                                    F.sub.3 C isopropyl 3-trifluoromethylphenyl                                    F.sub.3 C isopropyl 4-trifluoromethylphenyl                                    F.sub.3 C isopropyl 2-trifluromethoxyphenyl                                    F.sub.3 C isopropyl 2-difluoromethoxyphenyl                                    F.sub.3 C isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            F.sub.3 C isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         F.sub.3 C isopropyl 2-trifluoromethylthiophenyl                                F.sub.3 C isopropyl 2-methylphenyl                                             F.sub.3 C isbpropyl 3-methylphenyl                                             F.sub.3 C isopropyl 4-methylphenyl                                             F.sub.3 C isopropyl 2,3-dimethylphenyl                                         F.sub.3 C isopropyl 2,4-dimethylphenyl                                         F.sub.3 C isopropyl 2,5-dimethylphenyl                                         F.sub.3 C isopropyl 2,6-dimethylphenyl                                         F.sub.3 C isopropyl 2,4,6-trimethylphenyl                                      F.sub.3 C isopropyl 2-ethylphenyl                                              F.sub.3 C isopropyl 3-ethylphenyl                                              F.sub.3 C isopropyl 4-ethylphenyl                                              F.sub.3 C isopropyl 2-methoxyphenyl                                            F.sub.3 C isopropyl 3-methoxyphenyl                                            F.sub.3 C isopropyl 4-methoxyphenyl                                            F.sub.3 C isopropyl 2-methylthiophenyl                                         F.sub.3 C isopropyl 2-nitrophenyl                                              F.sub.3 C isopropyl 2-cyanophenyl                                              F.sub.2 ClC                                                                              ethyl     ethyl                                                      F.sub.2 ClC                                                                              ethyl     cyclohexyl                                                 F.sub.2 ClC                                                                              n-propyl  n-propyl                                                   F.sub.2 ClC                                                                              n-propyl  cyclopropyl                                                F.sub.2 ClC                                                                              n-propyl  cyclopentyl                                                F.sub.2 ClC                                                                              allyl     allyl                                                      F.sub.2 ClC                                                                              propargyl propargyl                                                  F.sub.2 ClC                                                                              methyl    phenyl                                                     F.sub.2 ClC                                                                              ethyl     phenyl                                                     F.sub.2 ClC                                                                              n-propyl  phenyl                                                     F.sub.2 ClC                                                                              isopropyl phenyl                                                     F.sub.2 ClC                                                                              n-butyl   phenyl                                                     F.sub.2 ClC                                                                              s-butyl   phenyl                                                     F.sub.2 ClC                                                                              isobutyl  phenyl                                                     F.sub.2 ClC                                                                              phenyl    phenyl                                                     F.sub.2 ClC                                                                              isopropyl 2-fluorophenyl                                             F.sub.2 ClC                                                                              isopropyl 3-fluorophenyl                                             F.sub.2 ClC                                                                              isopropyl 4-fluorophenyl                                             F.sub.2 ClC                                                                              isopropyl 2-chlorophenyl                                             F.sub.2 ClC                                                                              isopropyl 3-chlorophenyl                                             F.sub.2 ClC                                                                              isopropyl 4-chlorophenyl                                             F.sub.2 ClC                                                                              isopropyl 2,3-dichlorophenyl                                         F.sub.2 ClC                                                                              isopropyl 2,4-dichlorophenyl                                         F.sub.2 ClC                                                                              isopropyl 2,5-dichlorophenyl                                         F.sub.2 ClC                                                                              isopropyl 2,6-dichlorophenyl                                         F.sub.2 ClC                                                                              isopropyl 3,4-dichlorophenyl                                         F.sub.2 ClC                                                                              isopropyl 3-5-dichlorophenyl                                         F.sub.2 ClC                                                                              isopropyl 2,4,6-trichlorophenyl                                      F.sub.2 ClC                                                                              isopropyl 2-chloro-3-methylphenyl                                    F.sub.2 ClC                                                                              isopropyl 2-chloro-4-methylphenyl                                    F.sub.2 ClC                                                                              isopropyl 2-chloro-5-methylphenyl                                    F.sub.2 ClC                                                                              isopropyl 2-chloro-6-methylphenyl                                    F.sub.2 ClC                                                                              isopropyl 3-chloro-4-methylphenyl                                    F.sub.2 ClC                                                                              isopropyl 3-chloro-4-trifluoromethylphenyl                           F.sub.2 ClC                                                                              isopropyl 3-chloro-4-trifluromethoxyphenyl                           F.sub.2 ClC                                                                              isopropyl 3-chloro-4-trifluoromethylthiophenyl                       F.sub.2 ClC                                                                              isopropyl 2-bromophenyl                                              F.sub.2 ClC                                                                              isopropyl 2-trifluoromethylphenyl                                    F.sub.2 ClC                                                                              isopropyl 3-trifluoromethylphenyl                                    F.sub.2 ClC                                                                              isopropyl 4-trifluoromethylphenyl                                    F.sub.2 ClC                                                                              isopropyl 2-trifluromethoxyphenyl                                    F.sub.2 ClC                                                                              isopropyl 2-difluoromethoxyphenyl                                    F.sub.2 ClC                                                                              isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            F.sub.2 ClC                                                                              isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         F.sub.2 ClC                                                                              isopropyl 2-trifluoromethylthiophenyl                                F.sub.2 ClC                                                                              isopropyl 2-methylphenyl                                             F.sub.2 ClC                                                                              isopropyl 3-methylphenyl                                             F.sub.2 ClC                                                                              isopropyl 4-methylphenyl                                             F.sub.2 ClC                                                                              isopropyl 2,3-dimethylphenyl                                         F.sub.2 ClC                                                                              isopropyl 2,4-dimethylphenyl                                         F.sub.2 ClC                                                                              isopropyl 2,5-dimethylphenyl                                         F.sub.2 ClC                                                                              isopropyl 2,6-dimethylphenyl                                         F.sub.2 ClC                                                                              isopropyl 2,4,6-trimethylphenyl                                      F.sub.2 ClC                                                                              isopropyl 2-ethylphenyl                                              F.sub.2 ClC                                                                              isopropyl 3-ethylphenyl                                              F.sub.2 ClC                                                                              isopropyl 4-ethylphenyl                                              F.sub.2 ClC                                                                              isopropyl 2-methoxyphenyl                                            F.sub.2 ClC                                                                              isopropyl 3-methoxyphenyl                                            F.sub.2 ClC                                                                              isopropyl 4-methoxyphenyl                                            F.sub.2 ClC                                                                              isopropyl 2-methylthiophenyl                                         F.sub.2 ClC                                                                              isopropyl 2-nitrophenyl                                              F.sub.2 ClC                                                                              isopropyl 2-cyanophenyl                                              CH.sub.3 CHCl                                                                            ethyl     ethyl                                                      CH.sub.3 CHCl                                                                            ethyl     cyclohexyl                                                 CH.sub.3 CHCl                                                                            n-propyl  n-propyl                                                   CH.sub.3 CHCl                                                                            n-propyl  cyclopropyl                                                CH.sub.3 CHCl                                                                            n-propyl  cyclopentyl                                                CH.sub.3 CHCl                                                                            allyl     allyl                                                      CH.sub.3 CHCl                                                                            propargyl propargyl                                                  CH.sub.3 CHCl                                                                            methyl    phenyl                                                     CH.sub.3 CHCl                                                                            ethyl     phenyl                                                     CH.sub.3 CHCl                                                                            n-propyl  phenyl                                                     CH.sub.3 CHCl                                                                            isopropyl phenyl                                                     CH.sub.3 CHCl                                                                            n-butyl   phenyl                                                     CH.sub.3 CHCl                                                                            s-butyl   phenyl                                                     CH.sub.3 CHCl                                                                            isobutyl  phenyl                                                     CH.sub.3 CHCl                                                                            phenyl    phenyl                                                     CH.sub.3 CHCl                                                                            isopropyl 2-fluorophenyl                                             CH.sub.3 CHCl                                                                            isopropyl 3-fluorophenyl                                             CH.sub.3 CHCl                                                                            isopropyl 4-fluorophenyl                                             CH.sub.3 CHCl                                                                            isopropyl 2-chlorophenyl                                             CH.sub.3 CHCl                                                                            isopropyl 3-chlorophenyl                                             CH.sub.3 CHCl                                                                            isopropyl 4-chlorophenyl                                             CH.sub.3 CHCl                                                                            isopropyl 2,3-dichlorophenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2,4-dichlorophenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2,5-dichlorophenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2,6-dichlorophenyl                                         CH.sub.3 CHCl                                                                            isopropyl 3,4-dichlorophenyl                                         CH.sub.3 CHCl                                                                            isopropyl 3,5-dichlorophenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2,4,6-trichlorophenyl                                      CH.sub.3 CHCl                                                                            isopropyl 2-chloro-3-methylphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 2-chloro-4-methylphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 2-chloro-5-methylphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 2-chloro-6-methylphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 3-chloro-4-methylphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 3-chloro-4-trifluoromethylphenyl                           CH.sub.3 CHCl                                                                            isopropyl 3-chloro-4-trifluromethoxyphenyl                           CH.sub.3 CHCl                                                                            isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CH.sub.3 CHCl                                                                            isopropyl 2-bromophenyl                                              CH.sub.3 CHCl                                                                            isopropyl 2-trifluoromethylphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 3-trifluoromethylphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 4-trifluoromethylphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 2-trifluromethoxyphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 2-difluoromethoxyphenyl                                    CH.sub.3 CHCl                                                                            isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CH.sub.3 CHCl                                                                            isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CH.sub.3 CHCl                                                                            isopropyl 2-trifluoromethylthiophenyl                                CH.sub.3 CHCl                                                                            isopropyl 2-methylphenyl                                             CH.sub.3 CHCl                                                                            isopropyl 3-methylphenyl                                             CH.sub.3 CHCl                                                                            isopropyl 4-methylphenyl                                             CH.sub.3 CHCl                                                                            isopropyl 2,3-dimethylphenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2,4-dimethylphenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2,5-dimethylphenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2,6-dimethylphenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2,4,6-trimethylphenyl                                      CH.sub.3 CHCl                                                                            isopropyl 2-ethylphenyl                                              CH.sub.3 CHCl                                                                            isopropyl 3-ethylphenyl                                              CH.sub.3 CHCl                                                                            isopropyl 4-ethylphenyl                                              CH.sub.3 CHCl                                                                            isopropyl 2-methoxyphenyl                                            CH.sub.3 CHCl                                                                            isopropyl 3-methoxyphenyl                                            CH.sub.3 CHCl                                                                            isopropyl 4-methoxyphenyl                                            CH.sub.3 CHCl                                                                            isopropyl 2-methylthiophenyl                                         CH.sub.3 CHCl                                                                            isopropyl 2-nitrophenyl                                              CH.sub.3 CHCl                                                                            isopropyl 2-cyanophenyl                                              CH.sub.3 CHBr                                                                            ethyl     ethyl                                                      CH.sub.3 CHBr                                                                            ethyl     cyclohexyl                                                 CH.sub.3 CHBr                                                                            n-propyl  n-propyl                                                   CH.sub.3 CHBr                                                                            n-propyl  cyclopropyl                                                CH.sub.3 CHBr                                                                            n-propyl  cyclopentyl                                                CH.sub.3 CHBr                                                                            allyl     allyl                                                      CH.sub.3 CHBr                                                                            propargyl propargyl                                                  CH.sub.3 CHBr                                                                            methyl    phenyl                                                     CH.sub.3 CHBr                                                                            ethyl     phenyl                                                     CH.sub.3 CHBr                                                                            n-propyl  phenyl                                                     CH.sub.3 CHBr                                                                            isopropyl phenyl                                                     CH.sub.3 CHBr                                                                            n-butyl   phenyl                                                     CH.sub.3 CHBr                                                                            s-butyl   phenyl                                                     CH.sub.3 CHBr                                                                            isobutyl  phenyl                                                     CH.sub.3 CHBr                                                                            phenyl    phenyl                                                     CH.sub.3 CHBr                                                                            isopropyl 2-fluorophenyl                                             CH.sub.3 CHBr                                                                            isopropyl 3-fluorophenyl                                             CH.sub.3 CHBr                                                                            isopropyl 4-fluorophenyl                                             CH.sub.3 CHBr                                                                            isopropyl 2-chlorophenyl                                             CH.sub.3 CHBr                                                                            isopropyl 3-chlorophenyl                                             CH.sub.3 CHBr                                                                            isopropyl 4-chlorophenyl                                             CH.sub.3 CHBr                                                                            isopropyl 2,3-dichlorophenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2,4-dichlorophenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2,5-dichlorophenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2,6-dichlorophenyl                                         CH.sub.3 CHBr                                                                            isopropyl 3,4-dichlorophenyl                                         CH.sub.3 CHBr                                                                            isopropyl 3,5-dichlorophenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2,4,6-trichlorophenyl                                      CH.sub.3 CHBr                                                                            isopropyl 2-chloro-3-methylphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 2-chloro-4-methylphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 2-chloro-5-methylphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 2-chloro-6-methylphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 3-chloro-4-methylphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 3-chloro-4-trifluoromethylphenyl                           CH.sub.3 CHBr                                                                            isopropyl 3-chloro-4-trifluromethoxyphenyl                           CH.sub.3 CHBr                                                                            isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CH.sub.3 CHBr                                                                            isopropyl 2-bromophenyl                                              CH.sub.3 CHBr                                                                            isopropyl 2-trifluoromethylphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 3-trifluoromethylphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 4-trifluoromethylphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 2-trifluromethoxyphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 2-difluoromethoxyphenyl                                    CH.sub.3 CHBr                                                                            isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CH.sub.3 CHBr                                                                            isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CH.sub.3 CHBr                                                                            isopropyl 2-trifluoromethylthiophenyl                                CH.sub.3 CHBr                                                                            isopropyl 2-methylphenyl                                             CH.sub.3 CHBr                                                                            isopropyl 3-methylphenyl                                             CH.sub.3 CHBr                                                                            isopropyl 4-methylphenyl                                             CH.sub.3 CHBr                                                                            isopropyl 2,3-dimethylphenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2,4-dimethylphenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2,5-dimethylphenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2,6-dimethylphenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2,4,6-trimethylphenyl                                      CH.sub.3 CHBr                                                                            isopropyl 2-ethylphenyl                                              CH.sub.3 CHBr                                                                            isopropyl 3-ethylphenyl                                              CH.sub.3 CHBr                                                                            isopropyl 4-ethylphenyl                                              CH.sub.3 CHBr                                                                            isopropyl 2-methoxyphenyl                                            CH.sub.3 CHBr                                                                            isopropyl 3-methoxyphenyl                                            CH.sub.3 CHBr                                                                            isopropyl 4-methoxyphenyl                                            CH.sub.3 CHBr                                                                            isopropyl 2-methylthiophenyl                                         CH.sub.3 CHBr                                                                            isopropyl 2-nitrophenyl                                              CH.sub.3 CHBr                                                                            isopropyl 2-cyanophenyl                                              CH.sub.3 CHF                                                                             ethyl     ethyl                                                      CH.sub.3 CHF                                                                             ethyl     cyclohexyl                                                 CH.sub.3 CHF                                                                             n-propyl  n-propyl                                                   CH.sub.3 CHF                                                                             n-propyl  cyclopropyl                                                CH.sub.3 CHF                                                                             n-propyl  cyclopentyl                                                CH.sub.3 CHF                                                                             allyl     allyl                                                      CH.sub.3 CHF                                                                             propargyl propargyl                                                  CH.sub.3 CHF                                                                             methyl    phenyl                                                     CH.sub.3 CHF                                                                             ethyl     phenyl                                                     CH.sub.3 CHF                                                                             n-propyl  phenyl                                                     CH.sub.3 CHF                                                                             isopropyl phenyl                                                     CH.sub.3 CHF                                                                             n-butyl   phenyl                                                     CH.sub.3 CHF                                                                             s-butyl   phenyl                                                     CH.sub.3 CHF                                                                             isobutyl  phenyl                                                     CH.sub.3 CHF                                                                             phenyl    phenyl                                                     CH.sub.3 CHF                                                                             isopropyl 2-fluorophenyl                                             CH.sub.3 CHF                                                                             isopropyl 3-fluorophenyl                                             CH.sub.3 CHF                                                                             isopropyl 4-fluorophenyl                                             CH.sub.3 CHF                                                                             isopropyl 2-chlorophenyl                                             CH.sub.3 CHF                                                                             isopropyl 3-chlorophenyl                                             CH.sub.3 CHF                                                                             isopropyl 4-chlorophenyl                                             CH.sub.3 CHF                                                                             isopropyl 2,3-dichlorophenyl                                         CH.sub.3 CHF                                                                             isopropyl 2,4-dichlorophenyl                                         CH.sub.3 CHF                                                                             isopropyl 2,5-dichlorophenyl                                         CH.sub.3 CHF                                                                             isopropyl 2,6-dichlorophenyl                                         CH.sub.3 CHF                                                                             isopropyl 3,4-dichlorophenyl                                         CH.sub.3 CHF                                                                             isopropyl 3,5-dichlorophenyl                                         CH.sub.3 CHF                                                                             isopropyl 2,4,6-trichlorophenyl                                      CH.sub.3 CHF                                                                             isopropyl 2-chloro-3-methylphenyl                                    CH.sub.3 CHF                                                                             isopropyl 2-chloro-4-methylphenyl                                    CH.sub.3 CHF                                                                             isopropyl 2-chloro-5-methylphenyl                                    CH.sub.3 CHF                                                                             isopropyl 2-chloro-6-methylphenyl                                    CH.sub.3 CHF                                                                             isopropyl 3-chloro-4-methylphenyl                                    CH.sub.3 CHF                                                                             isopropyl 3-chloro-4-trifluoromethylphenyl                           CH.sub.3 CHF                                                                             isopropyl 3-chloro-4-trifluromethoxyphenyl                           CH.sub.3 CHF                                                                             isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CH.sub.3 CHF                                                                             isopropyl 2-bromophenyl                                              CH.sub.3 CHF                                                                             isopropyl 2-trifluoromethylphenyl                                    CH.sub.3 CHF                                                                             isopropyl 3-trifluoromethylphenyl                                    CH.sub.3 CHF                                                                             isopropyl 4-trifluoromethylphenyl                                    CH.sub.3 CHF                                                                             isopropyl 2-trifluromethoxyphenyl                                    CH.sub.3 CHF                                                                             isopropyl 2-difluoromethoxyphenyl                                    CH.sub.3 CHF                                                                             isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CH.sub.3 CHF                                                                             isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CH.sub.3 CHF                                                                             isopropyl 2-trifluoromethylthiophenyl                                CH.sub.3 CHF                                                                             isopropyl 2-methylphenyl                                             CH.sub.3 CHF                                                                             isopropyl 3-methylphenyl                                             CH.sub.3 CHF                                                                             isopropyl 4-methylphenyl                                             CH.sub.3 CHF                                                                             isopropyl 2,3-dimethylphenyl                                         CH.sub.3 CHF                                                                             isopropyl 2,4-dimethylphenyl                                         CH.sub.3 CHF                                                                             isopropyl 2,5-dimethylphenyl                                         CH.sub.3 CHF                                                                             isopropyl 2,6-dimethylphenyl                                         CH.sub.3 CHF                                                                             isopropyl 2,4,6-trimethylphenyl                                      CH.sub.3 CHF                                                                             isopropyl 2-ethylphenyl                                              CH.sub.3 CHF                                                                             isopropyl 3-ethylphenyl                                              CH.sub.3 CHF                                                                             isopropyl 4-ethylphenyl                                              CH.sub.3 CHF                                                                             isopropyl 2-methoxyphenyl                                            CH.sub.3 CHF                                                                             isopropyl 3-methoxyphenyl                                            CH.sub.3 CHF                                                                             isopropyl 4-methoxyphenyl                                            CH.sub.3 CHF                                                                             isopropyl 2-methylthiophenyl                                         CH.sub.3 CHF                                                                             isopropyl 2-nitrophenyl                                              CH.sub.3 CHF                                                                             isopropyl 2-cyanophenyl                                              ClCH.sub.2 CH.sub.2                                                                      ethyl     ethyl                                                      ClCH.sub.2 CH.sub.2                                                                      ethyl     cyclohexyl                                                 ClCH.sub.2 CH.sub.2                                                                      n-propyl  n-propyl                                                   ClCH.sub.2 CH.sub.2                                                                      n-propyl  cyclopropyl                                                ClCH.sub.2 CH.sub.2                                                                      n-propyl  cyclopentyl                                                ClCH.sub.2 CH.sub.2                                                                      allyl     allyl                                                      ClCH.sub.2 CH.sub.2                                                                      propargyl propargyl                                                  ClCH.sub.2 CH.sub.2                                                                      methyl    phenyl                                                     ClCH.sub.2 CH.sub.2                                                                      ethyl     phenyl                                                     ClCH.sub.2 CH.sub.2                                                                      n-propyl  phenyl                                                     ClCH.sub.2 CH.sub.2                                                                      isopropyl phenyl                                                     ClCH.sub.2 CH.sub.2                                                                      n-butyl   phenyl                                                     ClCH.sub.2 CH.sub.2                                                                      s-butyl   phenyl                                                     ClCH.sub.2 CH.sub.2                                                                      isobutyl  phenyl                                                     ClCH.sub.2 CH.sub.2                                                                      phenyl    phenyl                                                     ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-fluorophenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-fluorophenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 4-fluorophenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-chlorophenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-chlorophenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 4-chlorophenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,3-dichlorophenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,4-dichlorophenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,5-dichlorophenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,6-dichlorophenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 3,4-dichlorophenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 3,5-dichlorophenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,4,6-trichlorophenyl                                      ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-chloro-3-methylphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-chloro-4-methylphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-chloro-5-methylphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-chloro-6-methylphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-chloro-4-methylphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-chloro-4-trifluoromethylphenyl                           ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-chloro-4-trifluromethoxyphenyl                           ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-chloro-4-trifluoromethylthiophenyl                       ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-bromophenyl                                              ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-trifluoromethylphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-trifluoromethylphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 4-trifluoromethylphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-trifluromethoxyphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-difluoromethoxyphenyl                                    ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-trifluoromethylthiophenyl                                ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-methylphenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-methylphenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 4-methylphenyl                                             ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,3-dimethylphenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,4-dimethylphenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,5-dimethylphenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,6-dimethylphenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2,4,6-trimethylphenyl                                      ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-ethylphenyl                                              ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-ethylphenyl                                              ClCH.sub.2 CH.sub.2                                                                      isopropyl 4-ethylphenyl                                              ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-methoxyphenyl                                            ClCH.sub.2 CH.sub.2                                                                      isopropyl 3-methoxyphenyl                                            ClCH.sub.2 CH.sub.2                                                                      isopropyl 4-methoxyphenyl                                            ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-methylthiophenyl                                         ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-nitrophenyl                                              ClCH.sub.2 CH.sub.2                                                                      isopropyl 2-cyanophenyl                                              BrCH.sub.2 CH.sub.2                                                                      ethyl     ethyl                                                      BrCH.sub.2 CH.sub.2                                                                      ethyl     cyclohexyl                                                 BrCH.sub.2 CH.sub.2                                                                      n-propyl  n-propyl                                                   BrCH.sub.2 CH.sub.2                                                                      n-propyl  cyclopropyl                                                BrCH.sub.2 CH.sub.2                                                                      n-propyl  cyclopentyl                                                BrCH.sub.2 CH.sub.2                                                                      allyl     allyl                                                      BrCH.sub.2 CH.sub.2                                                                      propargyl propargyl                                                  BrCH.sub.2 CH.sub.2                                                                      methyl    phenyl                                                     BrCH.sub.2 CH.sub.2                                                                      ethyl     phenyl                                                     BrCH.sub.2 CH.sub.2                                                                      n-propyl  phenyl                                                     BrCH.sub.2 CH.sub.2                                                                      isopropyl phenyl                                                     BrCH.sub.2 CH.sub.2                                                                      n-butyl   phenyl                                                     BrCH.sub.2 CH.sub.2                                                                      s-butyl   phenyl                                                     BrCH.sub.2 CH.sub.2                                                                      isobutyl  phenyl                                                     BrCH.sub.2 CH.sub.2                                                                      phenyl    phenyl                                                     BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-fluorophenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-fluorophenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 4-fluorophenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-chlorophenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-chlorophenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 4-chlorophenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,3-dichlorophenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,4-dichlorophenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,5-dichlorophenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,6-dichlorophenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 3,4-dichlorophenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 3,5-dichlorophenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,4,6-trichlorophenyl                                      BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-chloro-3-methylphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-chloro-4-methylphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-chloro-5-methylphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-chloro-6-methylphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-chloro-4-methylphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-chloro-4-trifluoromethylphenyl                           BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-chloro-4-trifluromethoxyphenyl                           BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-chloro-4-trifluoromethylthiophenyl                       BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-bromophenyl                                              BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-trifluoromethylphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-trifluoromethylphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 4-trifluoromethylphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-trifluromethoxyphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-difluoromethoxyphenyl                                    BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-trifluoromethylthiophenyl                                BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-methylphenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-methylphenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 4-methylphenyl                                             BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,3-dimethylphenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,4-dimethylphenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,5-dimethylphenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,6-dimethylphenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2,4,6-trimethylphenyl                                      BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-ethylphenyl                                              BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-ethylphenyl                                              BrCH.sub.2 CH.sub.2                                                                      isopropyl 4-ethylphenyl                                              BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-methoxyphenyl                                            BrCH.sub.2 CH.sub.2                                                                      isopropyl 3-methoxyphenyl                                            BrCH.sub.2 CH.sub.2                                                                      isopropyl 4-methoxyphenyl                                            BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-methylthiophenyl                                         BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-nitrophenyl                                              BrCH.sub.2 CH.sub.2                                                                      isopropyl 2-cyanophenyl                                              FCH.sub.2 CH.sub.2                                                                       ethyl     ethyl                                                      FCH.sub.2 CH.sub.2                                                                       ethyl     cyclohexyl                                                 FCH.sub.2 CH.sub.2                                                                       n-propyl  n-propyl                                                   FCH.sub.2 CH.sub.2                                                                       n-propyl  cyclopropyl                                                FCH.sub.2 CH.sub.2                                                                       n-propyl  cyclopentyl                                                FCH.sub.2 CH.sub.2                                                                       allyl     allyl                                                      FCH.sub.2 CH.sub.2                                                                       propargyl propargyl                                                  FCH.sub.2 CH.sub.2                                                                       methyl    phenyl                                                     FCH.sub.2 CH.sub.2                                                                       ethyl     phenyl                                                     FCH.sub.2 CH.sub.2                                                                       n-propyl  phenyl                                                     FCH.sub.2 CH.sub.2                                                                       isopropyl phenyl                                                     FCH.sub.2 CH.sub.2                                                                       n-butyl   phenyl                                                     FCH.sub.2 CH.sub.2                                                                       s-butyl   phenyl                                                     FCH.sub.2 CH.sub.2                                                                       isobutyl  phenyl                                                     FCH.sub.2 CH.sub.2                                                                       phenyl    phenyl                                                     FCH.sub.2 CH.sub.2                                                                       isopropyl 2-fluorophenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 3-fluorophenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 4-fluorophenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 2-chlorophenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 3-chlorophenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 4-chlorophenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 2,3-dichlorophenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2,4-dichlorophenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2,5-dichlorophenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2,6-dichlorophenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 3,4-dichlorophenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 3,5-dichlorophenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2,4,6-trichlorophenyl                                      FCH.sub.2 CH.sub.2                                                                       isopropyl 2-chloro-3-methylphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 2-chloro-4-methylphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 2-chloro-5-methylphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 2-chloro-6-methylphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 3-chloro-4-methylphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 3-chloro-4-trifluoromethylphenyl                           FCH.sub.2 CH.sub.2                                                                       isopropyl 3-chloro-4-trifluromethoxyphenyl                           FCH.sub.2 CH.sub.2                                                                       isopropyl 3-chloro-4-trifluoromethylthiophenyl                       FCH.sub.2 CH.sub.2                                                                       isopropyl 2-bromophenyl                                              FCH.sub.2 CH.sub.2                                                                       isopropyl 2-trifluoromethylphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 3-trifluoromethylphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 4-trifluoromethylphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 2-trifluromethoxyphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 2-difluoromethoxyphenyl                                    FCH.sub.2 CH.sub.2                                                                       isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            FCH.sub.2 CH.sub.2                                                                       isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2-trifluoromethylthiophenyl                                FCH.sub.2 CH.sub.2                                                                       isopropyl 2-methylphenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 3-methylphenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 4-methylphenyl                                             FCH.sub.2 CH.sub.2                                                                       isopropyl 2,3-dimethylphenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2,4-dimethylphenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2,5-dimethylphenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2,6-dimethylphenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2,4,6-trimethylphenyl                                      FCH.sub.2 CH.sub.2                                                                       isopropyl 2-ethylphenyl                                              FCH.sub.2 CH.sub.2                                                                       isopropyl 3-ethylphenyl                                              FCH.sub.2 CH.sub.2                                                                       isopropyl 4-ethylphenyl                                              FCH.sub.2 CH.sub.2                                                                       isopropyl 2-methoxyphenyl                                            FCH.sub.2 CH.sub.2                                                                       isopropyl 3-methoxyphenyl                                            FCH.sub.2 CH.sub.2                                                                       isopropyl 4-methoxyphenyl                                            FCH.sub.2 CH.sub.2                                                                       isopropyl 2-methylthiophenyl                                         FCH.sub.2 CH.sub.2                                                                       isopropyl 2-nitrophenyl                                              FCH.sub.2 CH.sub.2                                                                       isopropyl 2-cyanophenyl                                              CH.sub.3 CCl.sub.2                                                                       ethyl     ethyl                                                      CH.sub.3 CCl.sub.2                                                                       ethyl     cyclohexyl                                                 CH.sub.3 CCl.sub.2                                                                       n-propyl  n-propyl                                                   CH.sub.3 CCl.sub.2                                                                       n-propyl  cyclopropyl                                                CH.sub.3 CCl.sub.2                                                                       n-propyl  cyclopentyl                                                CH.sub.3 CCl.sub.2                                                                       allyl     allyl                                                      CH.sub.3 CCl.sub.2                                                                       propargyl propargyl                                                  CH.sub.3 CCl.sub.2                                                                       methyl    phenyl                                                     CH.sub.3 CCl.sub.2                                                                       ethyl     phenyl                                                     CH.sub.3 CCl.sub.2                                                                       n-propyl  phenyl                                                     CH.sub.3 CCl.sub.2                                                                       isopropyl phenyl                                                     CH.sub.3 CCl.sub.2                                                                       n-butyl   phenyl                                                     CH.sub.3 CCl.sub.2                                                                       s-butyl   phenyl                                                     CH.sub.3 CCl.sub.2                                                                       isobutyl  phenyl                                                     CH.sub.3 CCl.sub.2                                                                       phenyl    phenyl                                                     CH.sub.3 CCl.sub.2                                                                       isopropyl 2-fluorophenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 3-fluorophenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 4-fluorophenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 2-chlorophenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 3-chlorophenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 4-chlorophenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 2,3-dichlorophenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2,4-dichlorophenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2,5-dichlorophenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2,6-dichlorophenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 3,4-dichlorophenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 3,5-dichlorophenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2,4,6-trichlorophenyl                                      CH.sub.3 CCl.sub.2                                                                       isopropyl 2-chloro-3-methylphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 2-chloro-4-methylphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 2-chloro-5-methylphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 2-chloro-6-methylphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 3-chloro-4-methylphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 3-chloro-4-trifluoromethylphenyl                           CH.sub.3 CCl.sub.2                                                                       isopropyl 3-chloro-4-trifluromethoxyphenyl                           CH.sub.3 CCl.sub.2                                                                       isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CH.sub.3 CCl.sub.2                                                                       isopropyl 2-bromophenyl                                              CH.sub.3 CCl.sub.2                                                                       isopropyl 2-trifluoromethylphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 3-trifluoromethylphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 4-trifluoromethylphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 2-trifluromethoxyphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 2-difluoromethoxyphenyl                                    CH.sub.3 CCl.sub.2                                                                       isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CH.sub.3 CCl.sub.2                                                                       isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2-trifluoromethylthiophenyl                                CH.sub.3 CCl.sub.2                                                                       isopropyl 2-methylphenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 3-methylphenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 4-methylphenyl                                             CH.sub.3 CCl.sub.2                                                                       isopropyl 2,3-dimethylphenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2,4-dimethylphenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2,5-dimethylphenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2,6-dimethylphenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2,4,6-trimethylphenyl                                      CH.sub.3 CCl.sub.2                                                                       isopropyl 2-ethylphenyl                                              CH.sub.3 CCl.sub.2                                                                       isopropyl 3-ethylphenyl                                              CH.sub.3 CCl.sub.2                                                                       isopropyl 4-ethylphenyl                                              CH.sub.3 CCl.sub.2                                                                       isopropyl 2-methoxyphenyl                                            CH.sub.3 CCl.sub.2                                                                       isopropyl 3-methoxyphenyl                                            CH.sub.3 CCl.sub.2                                                                       isopropyl 4-methoxyphenyl                                            CH.sub.3 CCl.sub.2                                                                       isopropyl 2-methylthiophenyl                                         CH.sub.3 CCl.sub.2                                                                       isopropyl 2-nitrophenyl                                              CH.sub.3 CCl.sub.2                                                                       isopropyl 2-cyanophenyl                                              ClCH.sub.2 CHCl                                                                          ethyl     ethyl                                                      ClCH.sub.2 CHCl                                                                          ethyl     cyclohexyl                                                 ClCH.sub.2 CHCl                                                                          n-propyl  n-propyl                                                   ClCH.sub.2 CHCl                                                                          n-propyl  cyclopropyl                                                ClCH.sub.2 CHCl                                                                          n-propyl  cyclopentyl                                                ClCH.sub.2 CHCl                                                                          allyl     allyl                                                      ClCH.sub.2 CHCl                                                                          propargyl propargyl                                                  ClCH.sub.2 CHCl                                                                          methyl    phenyl                                                     ClCH.sub.2 CHCl                                                                          ethyl     phenyl                                                     ClCH.sub.2 CHCl                                                                          n-propyl  phenyl                                                     ClCH.sub.2 CHCl                                                                          isopropyl phenyl                                                     ClCH.sub.2 CHCl                                                                          n-butyl   phenyl                                                     ClCH.sub.2 CHCl                                                                          s-butyl   phenyl                                                     ClCH.sub.2 CHCl                                                                          isobutyl  phenyl                                                     ClCH.sub.2 CHCl                                                                          phenyl    phenyl                                                     ClCH.sub.2 CHCl                                                                          isopropyl 2-fluorophenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 3-fluorophenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 4-fluorophenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 2-chlorophenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 3-chlorophenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 4-chlorophenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 2,3-dichlorophenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2,4-dichlorophenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2,5-dichlorophenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2,6-dichlorophenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 3,4-dichlorophenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 3,5-dichlorophenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2,4,6-trichlorophenyl                                      ClCH.sub.2 CHCl                                                                          isopropyl 2-chloro-3-methylphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 2-chloro-4-methylphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 2-chloro-5-methylphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 2-chloro-6-methylphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 3-chloro-4-methylphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 3-chloro-4-trifluoromethylphenyl                           ClCH.sub.2 CHCl                                                                          isopropyl 3-chloro-4-trifluromethoxyphenyl                           ClCH.sub.2 CHCl                                                                          isopropyl 3-chloro-4-trifluoromethylthiophenyl                       ClCH.sub.2 CHCl                                                                          isopropyl 2-bromophenyl                                              ClCH.sub.2 CHCl                                                                          isopropyl 2-trifluoromethylphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 3-trifluoromethylphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 4-trifluoromethylphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 2-trifluromethoxyphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 2-difluoromethoxyphenyl                                    ClCH.sub.2 CHCl                                                                          isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            ClCH.sub.2 CHCl                                                                          isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         ClCH.sub.2 CHCl                                                                          isopropyl 2-trifluoromethylthiophenyl                                ClCH.sub.2 CHCl                                                                          isopropyl 2-methylphenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 3-methylphenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 4-methylphenyl                                             ClCH.sub.2 CHCl                                                                          isopropyl 2,3-dimethylphenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2,4-dimethylphenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2,5-dimethylphenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2,6-dimethylphenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2,4,6-trimethylphenyl                                      ClCH.sub.2 CHCl                                                                          isopropyl 2-ethylphenyl                                              ClCH.sub.2 CHCl                                                                          isopropyl 3-ethylphenyl                                              ClCH.sub.2 CHCl                                                                          isopropyl 4-ethylphenyl                                              ClCH.sub.2 CHCl                                                                          isopropyl 2-methoxyphenyl                                            ClCH.sub.2 CHCl                                                                          isopropyl 3-methoxyphenyl                                            ClCH.sub.2 CHCl                                                                          isopropyl 4-methoxyphenyl                                            ClCH.sub.2 CHCl                                                                          isopropyl 2-methylthiophenyl                                         ClCH.sub.2 CHCl                                                                          isopropyl 2-nitrophenyl                                              ClCH.sub.2 CHCl                                                                          isopropyl 2-cyanophenyl                                              BrCH.sub.2 CHBr                                                                          ethyl     ethyl                                                      BrCH.sub.2 CHBr                                                                          ethyl     cyclohexyl                                                 BrCH.sub.2 CHBr                                                                          n-propyl  n-propyl                                                   BrCH.sub.2 CHBr                                                                          n-propyl  cyclopropyl                                                BrCH.sub.2 CHBr                                                                          n-propyl  cyclopentyl                                                BrCH.sub.2 CHBr                                                                          allyl     allyl                                                      BrCH.sub.2 CHBr                                                                          propargyl propargyl                                                  BrCH.sub.2 CHBr                                                                          methyl    phenyl                                                     BrCH.sub.2 CHBr                                                                          ethyl     phenyl                                                     BrCH.sub.2 CHBr                                                                          n-propyl  phenyl                                                     BrCH.sub.2 CHBr                                                                          isopropyl phenyl                                                     BrCH.sub.2 CHBr                                                                          n-butyl   phenyl                                                     BrCH.sub.2 CHBr                                                                          s-butyl   phenyl                                                     BrCH.sub.2 CHBr                                                                          isobutyl  phenyl                                                     BrCH.sub.2 CHBr                                                                          phenyl    phenyl                                                     BrCH.sub.2 CHBr                                                                          isopropyl 2-fluorophenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 3-fluorophenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 4-fluorophenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 2-chlorophenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 3-chlorophenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 4-chlorophenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 2,3-dichlorophenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2,4-dichlorophenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2,5-dichlorophenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2,6-dichlorophenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 3,4-dichlorophenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 3,5-dichlorophenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2,4,6-trichlorophenyl                                      BrCH.sub.2 CHBr                                                                          isopropyl 2-chloro-3-methylphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 2-chloro-4-methylphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 2-chloro-5-methylphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 2-chloro-6-methylphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 3-chloro-4-methylphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 3-chloro-4-trifluoromethylphenyl                           BrCH.sub.2 CHBr                                                                          isopropyl 3-chloro-4-trifluromethoxyphenyl                           BrCH.sub.2 CHBr                                                                          isopropyl 3-chloro-4-trifluoromethylthiophenyl                       BrCH.sub.2 CHBr                                                                          isopropyl 2-bromophenyl                                              BrCH.sub.2 CHBr                                                                          isopropyl 2-trifluoromethylphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 3-trifluoromethylphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 4-trifluoromethylphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 2-trifluoromethoxyphenyl                                   BrCH.sub.2 CHBr                                                                          isopropyl 2-difluoromethoxyphenyl                                    BrCH.sub.2 CHBr                                                                          isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            BrCH.sub.2 CHBr                                                                          isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         BrCH.sub.2 CHBr                                                                          isopropyl 2-trifluoromethylthiophenyl                                BrCH.sub.2 CHBr                                                                          isopropyl 2-methylphenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 3-methylphenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 4-methylphenyl                                             BrCH.sub.2 CHBr                                                                          isopropyl 2,3-dimethylphenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2,4-dimethylphenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2,5-dimethylphenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2,6-dimethylphenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2,4,6-trimethylphenyl                                      BrCH.sub.2 CHBr                                                                          isopropyl 2-ethylphenyl                                              BrCH.sub.2 CHBr                                                                          isopropyl 3-ethylphenyl                                              BrCH.sub.2 CHBr                                                                          isopropyl 4-ethylphenyl                                              BrCH.sub.2 CHBr                                                                          isopropyl 2-methoxyphenyl                                            BrCH.sub.2 CHBr                                                                          isopropyl 3-methoxyphenyl                                            BrCH.sub.2 CHBr                                                                          isopropyl 4-methoxyphenyl                                            BrCH.sub.2 CHBr                                                                          isopropyl 2-methylthiophenyl                                         BrCH.sub.2 CHBr                                                                          isopropyl 2-nitrophenyl                                              BrCH.sub.2 CHBr                                                                          isopropyl 2-cyanophenyl                                              FCH.sub.2 CHF                                                                            ethyl     ethyl                                                      FCH.sub.2 CHF                                                                            ethyl     cyclohexyl                                                 FCH.sub.2 CHF                                                                            n-propyl  n-propyl                                                   FCH.sub.2 CHF                                                                            n-propyl  cyclopropyl                                                FCH.sub.2 CHF                                                                            n-propyl  cyclopentyl                                                FCH.sub.2 CHF                                                                            allyl     allyl                                                      FCH.sub.2 CHF                                                                            propargyl propargyl                                                  FCH.sub.2 CHF                                                                            methyl    phenyl                                                     FCH.sub.2 CHF                                                                            ethyl     phenyl                                                     FCH.sub.2 CHF                                                                            n-propyl  phenyl                                                     FCH.sub.2 CHF                                                                            isopropyl phenyl                                                     FCH.sub.2 CHF                                                                            n-butyl   phenyl                                                     FCH.sub.2 CHF                                                                            s-butyl   phenyl                                                     FCH.sub.2 CHF                                                                            isobutyl  phenyl                                                     FCH.sub.2 CHF                                                                            phenyl    phenyl                                                     FCH.sub.2 CHF                                                                            isopropyl 2-fluorophenyl                                             FCH.sub.2 CHF                                                                            isopropyl 3-fluorophenyl                                             FCH.sub.2 CHF                                                                            isopropyl 4-fluorophenyl                                             FCH.sub.2 CHF                                                                            isopropyl 2-chlorophenyl                                             FCH.sub.2 CHF                                                                            isopropyl 3-chlorophenyl                                             FCH.sub.2 CHF                                                                            isopropyl 4-chlorophenyl                                             FCH.sub.2 CHF                                                                            isopropyl 2,3-dichlorophenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2,4-dichlorophenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2,5-dichlorophenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2,6-dichlorophenyl                                         FCH.sub.2 CHF                                                                            isopropyl 3,4-dichlorophenyl                                         FCH.sub.2 CHF                                                                            isopropyl 3,5-dichlorophenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2,4,6-trichlorophenyl                                      FCH.sub.2 CHF                                                                            isopropyl 2-chloro-3-methylphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 2-chloro-4-methylphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 2-chloro-5-methylphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 2-chloro-6-methylphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 3-chloro-4-methylphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 3-chloro-4-trifluoromethylphenyl                           FCH.sub.2 CHF                                                                            isopropyl 3-chloro-4-trifluromethoxyphenyl                           FCH.sub.2 CHF                                                                            isopropyl 3-chloro-4-trifluoromethylthiophenyl                       FCH.sub.2 CHF                                                                            isopropyl 2-bromophenyl                                              FCH.sub.2 CHF                                                                            isopropyl 2-trifluoromethylphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 3-trifluoromethylphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 4-trifluoromethylphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 2-trifluromethoxyphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 2-difluoromethoxyphenyl                                    FCH.sub.2 CHF                                                                            isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            FCH.sub.2 CHF                                                                            isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         FCH.sub.2 CHF                                                                            isopropyl 2-trifluoromethylthiophenyl                                FCH.sub.2 CHF                                                                            isopropyl 2-methylphenyl                                             FCH.sub.2 CHF                                                                            isopropyl 3-methylphenyl                                             FCH.sub.2 CHF                                                                            isopropyl 4-methylphenyl                                             FCH.sub.2 CHF                                                                            isopropyl 2,3-dimethylphenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2,4-dimethylphenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2,5-dimethylphenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2,6-dimethylphenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2,4,6-trimethylphenyl                                      FCH.sub.2 CHF                                                                            isopropyl 2-ethylphenyl                                              FCH.sub.2 CHF                                                                            isopropyl 3-ethylphenyl                                              FCH.sub.2 CHF                                                                            isopropyl 4-ethylphenyl                                              FCH.sub.2 CHF                                                                            isopropyl 2-methoxyphenyl                                            FCH.sub.2 CHF                                                                            isopropyl 3-methoxyphenyl                                            FCH.sub.2 CHF                                                                            isopropyl 4-methoxyphenyl                                            FCH.sub.2 CHF                                                                            isopropyl 2-methylthiophenyl                                         FCH.sub.2 CHF                                                                            isopropyl 2-nitrophenyl                                              FCH.sub.2 CHF                                                                            isopropyl 2-cyanophenyl                                              CCl.sub.3 CH.sub.2                                                                       ethyl     ethyl                                                      CCl.sub.3 CH.sub.2                                                                       ethyl     cyclohexyl                                                 CCl.sub.3 CH.sub.2                                                                       n-propyl  n-propyl                                                   CCl.sub.3 CH.sub.2                                                                       n-propyl  cyclopropyl                                                CCl.sub.3 CH.sub.2                                                                       n-propyl  cyclopentyl                                                CCl.sub.3 CH.sub.2                                                                       allyl     allyl                                                      CCl.sub.3 CH.sub.2                                                                       propargyl propargyl                                                  CCl.sub.3 CH.sub.2                                                                       methyl    phenyl                                                     CCl.sub.3 CH.sub.2                                                                       ethyl     phenyl                                                     CCl.sub.3 CH.sub.2                                                                       n-propyl  phenyl                                                     CCl.sub.3 CH.sub.2                                                                       isopropyl phenyl                                                     CCl.sub.3 CH.sub.2                                                                       n-butyl   phenyl                                                     CCl.sub.3 CH.sub.2                                                                       s-butyl   phenyl                                                     CCl.sub.3 CH.sub.2                                                                       isobutyl  phenyl                                                     CCl.sub.3 CH.sub.2                                                                       phenyl    phenyl                                                     CCl.sub.3 CH.sub.2                                                                       isopropyl 2-fluorophenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 3-fluorophenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 4-fluorophenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 2-chlorophenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 3-chlorophenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 4-chlorophenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 2,3-dichlorophenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2,4-dichlorophenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2,5-dichlorophenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2,6-dichlorophenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 3,4-dichlorophenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 3,5-dichlorophenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2,4,6-trichlorophenyl                                      CCl.sub.3 CH.sub.2                                                                       isopropyl 2-chloro-3-methylphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 2-chloro-4-methylphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 2-chloro-5-methylphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 2-chloro-6-methylphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 3-chloro-4-methylphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 3 chloro-4-trifluoromethylphenyl                           CCl.sub.3 CH.sub.2                                                                       isopropyl 3-chloro-4-trifluromethoxyphenyl                           CCl.sub.3 CH.sub.2                                                                       isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CCl.sub.3 CH.sub.2                                                                       isopropyl 2-bromophenyl                                              CCl.sub.3 CH.sub.2                                                                       isopropyl 2-trifluoromethylphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 3-trifluoromethylphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 4-trifluoromethylphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 2-trifluromethoxyphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 2-difluoromethoxyphenyl                                    CCl.sub.3 CH.sub.2                                                                       isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CCl.sub.3 CH.sub.2                                                                       isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2-trifluoromethylthiophenyl                                CCl.sub.3 CH.sub.2                                                                       isopropyl 2-methylphenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 3-methylphenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 4-methylphenyl                                             CCl.sub.3 CH.sub.2                                                                       isopropyl 2,3-dimethylphenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2,4-dimethylphenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2,6-dimethylphenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2,4,6-trimethylphenyl                                      CCl.sub.3 CH.sub.2                                                                       isopropyl 2-ethylphenyl                                              CCl.sub.3 CH.sub.2                                                                       isopropyl 3-ethylphenyl                                              CCl.sub.3 CH.sub.2                                                                       isopropyl 4-ethylphenyl                                              CCl.sub.3 CH.sub.2                                                                       isopropyl 2-methoxyphenyl                                            CCl.sub.3 CH.sub.2                                                                       isopropyl 3-methoxyphenyl                                            CCl.sub.3 CH.sub.2                                                                       isopropyl 4-methoxyphenyl                                            CCl.sub.3 CH.sub.2                                                                       isopropyl 2-methylthiophenyl                                         CCl.sub.3 CH.sub.2                                                                       isopropyl 2-nitrophenyl                                              CCl.sub.3 CH.sub.2                                                                       isopropyl 2-cyanophenyl                                              CCl.sub.3 CH.sub.2                                                                       isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CF.sub.3 CH.sub.2                                                                        ethyl     ethyl                                                      CF.sub.3 CH.sub.2                                                                        ethyl     cyclohexyl                                                 CF.sub.3 CH.sub.2                                                                        n-propyl  n-propyl                                                   CF.sub.3 CH.sub.2                                                                        n-propyl  cyclopropyl                                                CF.sub.3 CH.sub.2                                                                        n-propyl  cyclopentyl                                                CF.sub.3 CH.sub.2                                                                        allyl     allyl                                                      CF.sub.3 CH.sub.2                                                                        propargyl propargyl                                                  CF.sub.3 CH.sub.2                                                                        methyl    phenyl                                                     CF.sub.3 CH.sub.2                                                                        ethyl     phenyl                                                     CF.sub.3 CH.sub.2                                                                        n-propyl  phenyl                                                     CF.sub.3 CH.sub.2                                                                        isopropyl phenyl                                                     CF.sub.3 CH.sub.2                                                                        n-butyl   phenyl                                                     CF.sub.3 CH.sub.2                                                                        s-butyl   phenyl                                                     CF.sub.3 CH.sub.2                                                                        isobutyl  phenyl                                                     CF.sub.3 CH.sub.2                                                                        phenyl    phenyl                                                     CF.sub.3 CH.sub.2                                                                        isopropyl 2-fluorophenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 3-fluorophenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 4-fluorophenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 2-chlorophenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 3-chlorophenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 4-chlorophenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 2,3-dichlorophenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 2,4-dichlorophenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 2,5-dichlorophenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 2,6-dichlorophenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 3,4-dichlorophenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 3,5-dichlorophenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 2,4,6-trichlorophenyl                                      CF.sub.3 CH.sub.2                                                                        isopropyl 2-chloro-3-methylphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 2-chloro-4-methylphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 2-chloro-5-methylphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 2-chloro-6-methylphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 3-chloro-4-methylphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 3-chloro-4-trifluoromethylphenyl                           CF.sub.3 CH.sub.2                                                                        isopropyl 3-chloro-4-trifluromethoxyphenyl                           CF.sub.3 CH.sub.2                                                                        isopropyl 2-bromophenyl                                              CF.sub.3 CH.sub.2                                                                        isopropyl 2-trifluoromethylphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 3-trifluoromethylphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 4-trifluoromethylphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 2-trifluromethoxyphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 2-difluoromethoxyphenyl                                    CF.sub.3 CH.sub.2                                                                        isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CF.sub.3 CH.sub.2                                                                        isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CF.sub.3 CH.sub.2                                                                        isopropyl 2-trifluoromethylthiophenyl                                CF.sub.3 CH.sub.2                                                                        isopropyl 2-methylphenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 3-methylphenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 4-methylphenyl                                             CF.sub.3 CH.sub.2                                                                        isopropyl 2,3-dimethylphenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 2,4-dimethylphenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 2,6-dimethylphenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 2,4,6-trimethylphenyl                                      CF.sub.3 CH.sub.2                                                                        isopropyl 2-ethylphenyl                                              CF.sub.3 CH.sub.2                                                                        isopropyl 3-ethylphenyl                                              CF.sub.3 CH.sub.2                                                                        isopropyl 4-ethylphenyl                                              CF.sub.3 CH.sub.2                                                                        isopropyl 2-methoxyphenyl                                            CF.sub.3 CH.sub.2                                                                        isopropyl 3-methoxyphenyl                                            CF.sub.3 CH.sub.2                                                                        isopropyl 4-methoxyphenyl                                            CF.sub.3 CH.sub.2                                                                        isopropyl 2-methylthiophenyl                                         CF.sub.3 CH.sub.2                                                                        isopropyl 2-nitrophenyl                                              CF.sub.3 CH.sub.2                                                                        isopropyl 2-cyanophenyl                                              CF.sub.3 CF.sub.2                                                                        ethyl     ethyl                                                      CF.sub.3 CF.sub.2                                                                        ethyl     cyclohexyl                                                 CF.sub.3 CF.sub.2                                                                        n-propyl  n-propyl                                                   CF.sub.3 CF.sub.2                                                                        n-propyl  cyclopropyl                                                CF.sub.3 CF.sub.2                                                                        n-propyl  cyclopentyl                                                CF.sub.3 CF.sub.2                                                                        allyl     allyl                                                      CF.sub.3 CF.sub.2                                                                        propargyl propargyl                                                  CF.sub.3 CF.sub.2                                                                        methyl    phenyl                                                     CF.sub.3 CF.sub.2                                                                        ethyl     phenyl                                                     CF.sub.3 CF.sub.2                                                                        n-propyl  phenyl                                                     CF.sub.3 CF.sub.2                                                                        isopropyl phenyl                                                     CF.sub.3 CF.sub.2                                                                        n-butyl   phenyl                                                     CF.sub.3 CF.sub.2                                                                        s-butyl   phenyl                                                     CF.sub.3 CF.sub.2                                                                        isobutyl  phenyl                                                     CF.sub.3 CF.sub.2                                                                        phenyl    phenyl                                                     CF.sub.3 CF.sub.2                                                                        isopropyl 2-fluorophenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 3-fluorophenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 4-fluorophenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 2-chlorophenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 3-chlorophenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 4-chlorophenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 2,3-dichlorophenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 2,4-dichlorophenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 2,5-dichlorophenyl                                         CCl.sub.3 CF.sub.2                                                                       isopropyl 2,6-dichlorophenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 3,4-dichlorophenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 3,5-dichlorophenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 2,4,6-trichlorophenyl                                      CF.sub.3 CF.sub.2                                                                        isopropyl 2-chloro-3-methylphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 2-chloro-4-methylphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 2-chloro-5-methylphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 2-chloro-6-methylphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 3-chloro-4-methylphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 3-chloro-4-trifluoromethylphenyl                           CF.sub.3 CF.sub.2                                                                        isopropyl 3-chloro-4-trifluromethoxyphenyl                           CF.sub.3 CF.sub.2                                                                        isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CF.sub.3 CF.sub.2                                                                        isopropyl 2-bromophenyl                                              CF.sub.3 CF.sub.2                                                                        isopropyl 2-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 3-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 4-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 2-trifluromethoxyphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 2-difluoromethoxyphenyl                                    CF.sub.3 CF.sub.2                                                                        isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CF.sub.3 CF.sub.2                                                                        isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CF.sub.3 CF.sub.2                                                                        isopropyl 2-methylphenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 3-methylphenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 4-methylphenyl                                             CF.sub.3 CF.sub.2                                                                        isopropyl 2,3-dimethylphenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 2,4-dimethylphenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 2,6-dimethylphenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 2,4,6-trimethylphenyl                                      CF.sub.3 CF.sub.2                                                                        isopropyl 2-ethylphenyl                                              CF.sub.3 CF.sub.2                                                                        isopropyl 3-ethylphenyl                                              CF.sub.3 CF.sub.2                                                                        isopropyl 4-ethylphenyl                                              CF.sub.3 CF.sub.2                                                                        isopropyl 2-methoxyphenyl                                            CF.sub.3 CF.sub.2                                                                        isopropyl 3-methoxyphenyl                                            CF.sub.3 CF.sub.2                                                                        isopropyl 4-methoxyphenyl                                            CF.sub.3 CF.sub.2                                                                        isopropyl 2-methylthiophenyl                                         CF.sub.3 CF.sub.2                                                                        isopropyl 2-nitrophenyl                                              CF.sub.3 CF.sub.2                                                                        isopropyl 2-cyanophenyl                                              ClCH.sub.2 CH.sub.2 CH.sub.2                                                             ethyl     ethyl                                                      ClCH.sub.2 CH.sub.2 CH.sub.2                                                             ethyl     cyclohexyl                                                 ClCH.sub.2 CH.sub.2 CH.sub.2                                                             n-propyl  n-propyl                                                   ClCH.sub.2 CH.sub.2 CH.sub.2                                                             n-propyl  cyclopropyl                                                ClCH.sub.2 CH.sub.2 CH.sub.2                                                             n-propyl  cyclopentyl                                                ClCH.sub.2 CH.sub.2 CH.sub.2                                                             allyl     allyl                                                      ClCH.sub.2 CH.sub.2 CH.sub.2                                                             propargyl propargyl                                                  ClCH.sub.2 CH.sub.2 CH.sub.2                                                             methyl    phenyl                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                             ethyl     phenyl                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                             n-propyl  phenyl                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl phenyl                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                             n-butyl   phenyl                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                             s-butyl   phenyl                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isobutyl  phenyl                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                             phenyl    phenyl                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-fluorophenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-fluorophenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 4-fluorophenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-chlorophenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-chlorophenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 4-chlorophenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,3-dichlorophenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,4-dichlorophenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,5-dichlorophenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,6-dichlorophenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3,4-dichlorophenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3,5-dichlorophenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,4,6-trichlorophenyl                                      ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-chloro-3-methylphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-chloro-4-methylphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-chloro-5-methylphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-chloro-6-methylphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-chloro-4-methylphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-chloro-4-trifluoromethylphenyl                           ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-chloro-4-trifluromethoxyphenyl                           ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-chloro-4-trifluoromethylthiophenyl                       ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-bromophenyl                                              ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-trifluoromethylphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-trifluoromethylphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 4-trifluoromethylphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-trifluromethoxyphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-difluoromethoxyphenyl                                    ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-methylphenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-methylphenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 4-methylphenyl                                             ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,3-dimethylphenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,4-dimethylphenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,6-dimethylphenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2,4,6-trimethylphenyl                                      ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-ethylphenyl                                              ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-ethylphenyl                                              ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 4-ethylphenyl                                              ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-methoxyphenyl                                            ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 3-methoxyphenyl                                            ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 4-methoxyphenyl                                            ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-methylthiophenyl                                         ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-nitrophenyl                                              ClCH.sub.2 CH.sub.2 CH.sub.2                                                             isopropyl 2-cyanophenyl                                              FCH.sub.2 CH.sub.2 CH.sub.2                                                              ethyl     ethyl                                                      FCH.sub.2 CH.sub.2 CH.sub.2                                                              ethyl     cyclohexyl                                                 FCH.sub.2 CH.sub.2 CH.sub.2                                                              n-propyl  n-propyl                                                   FCH.sub.2 CH.sub.2 CH.sub.2                                                              n-propyl  cyclopropyl                                                FCH.sub.2 CH.sub.2 CH.sub.2                                                              n-propyl  cyclopentyl                                                FCH.sub.2 CH.sub.2 CH.sub.2                                                              allyl     allyl                                                      FCH.sub.2 CH.sub.2 CH.sub.2                                                              propargyl propargyl                                                  FCH.sub.2 CH.sub.2 CH.sub.2                                                              methyl    phenyl                                                     FCH.sub.2 CH.sub.2 CH.sub.2                                                              ethyl     phenyl                                                     FCH.sub.2 CH.sub.2 CH.sub.2                                                              n-propyl  phenyl                                                     FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl phenyl                                                     FCH.sub.2 CH.sub.2 CH.sub.2                                                              n-butyl   phenyl                                                     FCH.sub.2 CH.sub.2 CH.sub.2                                                              s-butyl   phenyl                                                     FCH.sub.2 CH.sub.2 CH.sub.2                                                              isobutyl  phenyl                                                     FCH.sub.2 CH.sub.2 CH.sub.2                                                              phenyl    phenyl                                                     FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-fluorophenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-fluorophenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 4-fluorophenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-chlorophenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-chlorophenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 4-chlorophenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,3-dichlorophenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,4-dichlorophenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,5-dichlorophenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,6-dichlorophenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3,4-dichlorophenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3,5-dichlorophenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,4,6-trichlorophenyl                                      FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-chloro-3-methylphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-chloro-4-methylphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-chloro-5-methylphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-chloro-6-methylphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-chloro-4-methylphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-chloro-4-trifluoromethylphenyl                           FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-chloro-4-trifluromethoxyphenyl                           FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-chloro-4-trifluoromethylthiophenyl                       FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-bromophenyl                                              FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-trifluoromethylphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-trifluoromethylphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 4-trifluoromethylphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-trifluromethoxyphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-difluoromethoxyphenyl                                    FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-methylphenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-methylphenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 4-methylphenyl                                             FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,3-dimethylphenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,4-dimethylphenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,6-dimethylphenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2,4,6-trimethylphenyl                                      FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-ethylphenyl                                              FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-ethylphenyl                                              FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 4-ethylphenyl                                              FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-methoxyphenyl                                            FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 3-methoxyphenyl                                            FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 4-methoxyphenyl                                            FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-methylthiophenyl                                         FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-nitrophenyl                                              FCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl 2-cyanophenyl                                              CF.sub.3 CF.sub.2 CH.sub.2                                                               ethyl     ethyl                                                      CF.sub.3 CF.sub.2 CH.sub.2                                                               ethyl     cyclohexyl                                                 CF.sub.3 CF.sub.2 CH.sub.2                                                               n-propyl  n-propyl                                                   CF.sub.3 CF.sub.2 CH.sub.2                                                               n-propyl  cyclopropyl                                                CF.sub.3 CF.sub.2 CH.sub.2                                                               n-propyl  cyclopentyl                                                CF.sub.3 CF.sub.2 CH.sub.2                                                               allyl     allyl                                                      CF.sub.3 CF.sub.2 CH.sub.2                                                               propargyl propargyl                                                  CF.sub.3 CF.sub.2 CH.sub.2                                                               methyl    phenyl                                                     CF.sub.3 CF.sub.2 CH.sub.2                                                               ethyl     phenyl                                                     CF.sub.3 CF.sub.2 CH.sub.2                                                               n-propyl  phenyl                                                     CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl phenyl                                                     CF.sub.3 CF.sub.2 CH.sub.2                                                               n-butyl   phenyl                                                     CF.sub.3 CF.sub.2 CH.sub.2                                                               s-butyl   phenyl                                                     CF.sub.3 CF.sub.2 CH.sub.2                                                               isobutyl  phenyl                                                     CF.sub.3 CF.sub.2 CH.sub.2                                                               phenyl    phenyl                                                     CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-fluorophenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-fluorophenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 4-fluorophenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-chlorophenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-chlorophenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 4-chlorophenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,3-dichlorophenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,4-dichlorophenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,5-dichlorophenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,6-dichlorophenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3,4-dichlorophenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3,5-dichlorophenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,4,6-trichlorophenyl                                      CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-chloro-3-methylphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-chloro-4-methylphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-chloro-5-methylphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-chloro-6-methylphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-chloro-4-methylphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-chloro-4-trifluoromethylphenyl                           CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-chloro-4-trifluromethoxyphenyl                           CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-bromophenyl                                              CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 4-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-trifluromethoxyphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-difluoromethoxyphenyl                                    CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-methylphenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-methylphenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 4-methylphenyl                                             CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,3-dimethylphenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,4-dimethylphenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,6-dimethylphenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2,4,6-trimethylphenyl                                      CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-ethylphenyl                                              CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-ethylphenyl                                              CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 4-ethylphenyl                                              CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-methoxyphenyl                                            CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 3-methoxyphenyl                                            CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 4-methoxyphenyl                                            CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-methylthiophenyl                                         CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-nitrophenyl                                              CF.sub.3 CF.sub.2 CH.sub.2                                                               isopropyl 2-cyanophenyl                                              CF.sub.3 CF.sub.2 CF.sub.2                                                               ethyl     ethyl                                                      CF.sub.3 CF.sub.2 CF.sub.2                                                               ethyl     cyclohexyl                                                 CF.sub.3 CF.sub.2 CF.sub.2                                                               n-propyl  n-propyl                                                   CF.sub.3 CF.sub.2 CF.sub.2                                                               n-propyl  cyclopropyl                                                CF.sub.3 CF.sub.2 CF.sub.2                                                               n-propyl  cyclopentyl                                                CF.sub.3 CF.sub.2 CF.sub.2                                                               allyl     allyl                                                      CF.sub.3 CF.sub.2 CF.sub.2                                                               propargyl propargyl                                                  CF.sub.3 CF.sub.2 CF.sub.2                                                               methyl    phenyl                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                               ethyl     phenyl                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                               n-propyl  phenyl                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl phenyl                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                               n-butyl   phenyl                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                               s-butyl   phenyl                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                               isobutyl  phenyl                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                               phenyl    phenyl                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-fluorophenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-fluorophenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 4-fluorophenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-chlorophenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-chlorophenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 4-chlorophenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,3-dichlorophenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,4-dichlorophenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,5-dichlorophenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,6-dichlorophenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3,4-dichlorophenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3,5-dichlorophenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,4,6-trichlorophenyl                                      CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-chloro-3-methylphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-chloro-4-methylphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-chloro-5-methylphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-chloro-6-methylphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-chloro-4-methylphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-chloro-4-trifluoromethylphenyl                           CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-chloro-4-trifluromethoxyphenyl                           CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-chloro-4-trifluoromethylthiophenyl                       CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-bromophenyl                                              CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 4-trifluoromethylphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-trifluromethoxyphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-difluoromethoxyphenyl                                    CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-(2,2,2-trifluoroethoxy)phenyl                            CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-(2,2,2-trifluoroethylthio)phenyl                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-methylphenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-methylphenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 4-methylphenyl                                             CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,3-dimethylphenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,4-dimethylphenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,6-dimethylphenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2,4,6-trimethylphenyl                                      CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-ethylphenyl                                              CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-ethylphenyl                                              CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 4-ethylphenyl                                              CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-methoxyphenyl                                            CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 3-methoxyphenyl                                            CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 4-methoxyphenyl                                            CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-methylthiophenyl                                         CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-nitrophenyl                                              CF.sub.3 CF.sub.2 CF.sub.2                                                               isopropyl 2-cyanophenyl                                              ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR7##                                                                      R.sup.1                                                                                      ##STR8##                                                         ______________________________________                                         ClCH.sub.2   piperidino                                                        ClCH.sub.2   2-methylpiperidino                                                ClCH.sub.2   indol-1-yl                                                        ClCH.sub.2   perhydroindol-1-yl                                                ClCH.sub.2   1,2,3,4-tetrahydroquinolin-1-yl                                   ClCH.sub.2   2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          BrCH.sub.2   piperidino                                                        BrCH.sub.2   2-methylpiperidino                                                BrCH.sub.2   indol-1-yl                                                        BrCH.sub.2   perhydroindol-1-yl                                                BrCH.sub.2   1,2,3,4-tetrahydroquinolin-1-yl                                   BrCH.sub.2   2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          FCH.sub.2    piperidino                                                        FCH.sub.2    2-methylpiperidino                                                FCH.sub.2    indol-1-yl                                                        FCH.sub.2    perhydroindol-1-yl                                                FCH.sub.2    1,2,3,4-tetrahydroquinolin-1-yl                                   FCH.sub.2    2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          Cl.sub.2 HC  piperidino                                                        Cl.sub.2 HC  2-methylpiperidino                                                Cl.sub.2 HC  indol-1-yl                                                        Cl.sub.2 HC  perhydroindol-1-yl                                                Cl.sub.2 HC  1,2,3,4-tetrahydroquinolin-1-yl                                   Cl.sub.2 HC  2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          F.sub.2 HC   piperidino                                                        F.sub.2 HC   2-methylpiperidino                                                F.sub.2 HC   indol-1-yl                                                        F.sub.2 HC   perhydroindol-1-yl                                                F.sub.2 HC   1,2,3,4-tetrahydroquinolin-1-yl                                   F.sub.2 HC   2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          Cl.sub.3 C   piperidino                                                        Cl.sub.3 C   2-methylpiperidino                                                Cl.sub.3 C   indol-1-yl                                                        Cl.sub.3 C   perhydroindol-1-yl                                                Cl.sub.3 C   1,2,3,4-tetrahydroquinolin-1-yl                                   Cl.sub.3 C   2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          F.sub.3 C    piperidino                                                        F.sub.3 C    2-methylpiperidino                                                F.sub.3 C    indol-1-yl                                                        F.sub.3 C    perhydroindol-1-yl                                                F.sub.3 C    1,2,3,4-tetrahydroquinolin-1-yl                                   F.sub.3 C    2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          F.sub.2 ClC  piperidino                                                        F.sub.2 ClC  2-methylpiperidino                                                F.sub.2 ClC  indol-1-yl                                                        F.sub.2 ClC  perhydroindol-1-yl                                                F.sub.2 ClC  1,2,3,4-tetrahydroquinolin-1-yl                                   F.sub.2 ClC  2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CH.sub.3 CHCl                                                                               piperidino                                                        CH.sub.3 CHCl                                                                               2-methylpiperidino                                                CH.sub.3 CHCl                                                                               indol-1-yl                                                        CH.sub.3 CHCl                                                                               perhydroindol-1-yl                                                CH.sub.3 CHCl                                                                               1,2,3,4-tetrahydroquinolin-l-yl                                   CH.sub.3 CHCl                                                                               2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CH.sub.3 CHBr                                                                               piperidino                                                        CH.sub.3 CHBr                                                                               2-methylpiperidino                                                CH.sub.3 CHBr                                                                               indol-1-yl                                                        CH.sub.3 CHBr                                                                               perhydroindol-1-yl                                                CH.sub.3 CHBr                                                                               1,2,3,4-tetrahydroquinolin-1-yl                                   CH.sub.3 CHBr                                                                               2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CH.sub.3 CHF piperidino                                                        CH.sub.3 CHF 2-methylpiperidino                                                CH.sub.3 CHF indol-1-yl                                                        CH.sub.3 CHF perhydroindol-1-yl                                                CH.sub.3 CHF 1,2,3,4-tetrahydroquinolin-1-yl                                   CH.sub.3 CHF 2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          ClCH.sub.2 CH.sub.2                                                                         piperidino                                                        ClCH.sub.2 CH.sub.2                                                                         2-methylpiperidino                                                ClCH.sub.2 CH.sub.2                                                                         indol-1-yl                                                        ClCH.sub.2 CH.sub.2                                                                         1,2,3,4-tetrahydroquinolin-1-yl                                   ClCH.sub.2 CH.sub.2                                                                         2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          BrCH.sub.2 CH.sub.2                                                                         piperidino                                                        BrCH.sub.2 CH.sub.2                                                                         2-methylpiperidino                                                BrCH.sub.2 CH.sub.2                                                                         indolin-1-yl                                                      BrCH.sub.2 CH.sub.2                                                                         1,2,3,4-tetrahydroquinolin-1-yl                                   BrCH.sub.2 CH.sub.2                                                                         2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          FCH.sub.2 CH.sub.2                                                                          piperidino                                                        FCH.sub.2 CH.sub.2                                                                          2-methylpiperidino                                                FCH.sub.2 CH.sub.2                                                                          indol-1-yl                                                        FCH.sub.2 CH.sub.2                                                                          1,2,3,4-tetrahydroquinolin-1-yl                                   FCH.sub.2 CH.sub.2                                                                          2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CH.sub.3 CCl.sub.2                                                                          piperidino                                                        CH.sub.3 CCl.sub.2                                                                          2-methylpiperidino                                                CH.sub.3 CCl.sub.2                                                                          indolin-1-yl                                                      CH.sub.3 CCl.sub.2                                                                          perhydroindol-1-yl                                                CH.sub.3 CCl.sub.2                                                                          1,2,3,4-tetrahydroquinolin-1-yl                                   CH.sub.3 CCl.sub.2                                                                          2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          ClCH.sub.2 CHCl                                                                             piperidino                                                        ClCH.sub.2 CHCl                                                                             2-methylpiperidino                                                ClCH.sub.2 CHCl                                                                             indol-1-yl                                                        ClCH.sub.2 CHCl                                                                             perhydroindol-1-yl                                                ClCH.sub.2 CHCl                                                                             1,2,3,4-tetrahydroquinolin-1-yl                                   ClCH.sub.2 CHCl                                                                             2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          BrCH.sub.2 CHBr                                                                             piperidino                                                        BrCH.sub.2 CHBr                                                                             2-methylpiperidino                                                BrCH.sub.2 CHBr                                                                             indol-1-yl                                                        BrCH.sub.2 CHBr                                                                             perhydroindol-1-yl                                                BrCH.sub.2 CHBr                                                                             1,2,3,4-tetrahydroquinolin-1-yl                                   BrCH.sub.2 CHBr                                                                             2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          FCH.sub.2 CHF                                                                               piperidino                                                        FCH.sub.2 CHF                                                                               2-methylpiperidino                                                FCH.sub.2 CHF                                                                               indol-1-yl                                                        FCH.sub.2 CHF                                                                               perhydroindol-1-yl                                                FCH.sub.2 CHF                                                                               1,2,3,4-tetrahydroquinolin-1-yl                                   FCH.sub.2 CHF                                                                               2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CCl.sub.3 CH.sub.2                                                                          piperidino                                                        CCl.sub.3 CH.sub.2                                                                          2-methylpiperidino                                                CCl.sub.3 CH.sub.2                                                                          indol-1-yl                                                        CCl.sub.3 CH.sub.2                                                                          perhydroindol-1-yl                                                CCl.sub.3 CH.sub.2                                                                          1,2,3,4-tetrahydroquinolin-1-yl                                   CCl.sub.3 CH.sub.2                                                                          2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CF.sub.3 CH.sub.2                                                                           piperidino                                                        CF.sub.3 CH.sub.2                                                                           2-methylpiperidino                                                CF.sub.3 CH.sub.2                                                                           indolin-1-yl                                                      CF.sub.3 CH.sub.2                                                                           perhydroindol-1-yl                                                CF.sub.3 CH.sub.2                                                                           1,2,3,4-tetrahydroquinolin-1-yl                                   CF.sub.3 CH.sub.2                                                                           2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CF.sub.3 CF.sub.2                                                                           piperidino                                                        CF.sub.3 CF.sub.2                                                                           2-methylpiperidino                                                CF.sub.3 CF.sub.2                                                                           indol-1-yl                                                        CF.sub.3 CF.sub.2                                                                           perhydroindol-1-yl                                                CF.sub.3 CF.sub.2                                                                           1,2,3,4-tetrahydroquinolin-1-yl                                   CF.sub.3 CF.sub.2                                                                           2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          ClCH.sub.2 CH.sub.2 CH.sub.2                                                                piperidino                                                        ClCH.sub.2 CH.sub.2 CH.sub.2                                                                2-methylpiperidino                                                ClCH.sub.2 CH.sub.2 CH.sub.2                                                                indol-1-yl                                                        ClCH.sub.2 CH.sub.2 CH.sub.2                                                                perhydroindol-1-yl                                                ClCH.sub.2 CH.sub.2 CH.sub.2                                                                1,2,3,4-tetrahydroquinolin-1-yl                                   ClCH.sub.2 CH.sub.2 CH.sub.2                                                                2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          FCH.sub.2 CH.sub.2 CH.sub.2                                                                 piperidino                                                        FCH.sub.2 CH.sub.2 CH.sub.2                                                                 2-methylpiperidino                                                FCH.sub.2 CH.sub.2 CH.sub.2                                                                 indol-1-yl                                                        FCH.sub.2 CH.sub.2 CH.sub.2                                                                 perhydroindol-1-yl                                                FCH.sub.2 CH.sub.2 CH.sub.2                                                                 1,2,3,4-tetrahydroquinolin-1-yl                                   FCH.sub.2 CH.sub.2 CH.sub.2                                                                 2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CF.sub.3 CF.sub.2 CH.sub.2                                                                  piperidino                                                        CF.sub.3 CF.sub.2 CH.sub.2                                                                  2-methylpiperidino                                                CF.sub.3 CF.sub.2 CH.sub.2                                                                  indol-1-yl                                                        CF.sub.3 CF.sub.2 CH.sub.2                                                                  perhydroindol-1-yl                                                CF.sub.3 CF.sub.2 CH.sub.2                                                                  1,2,3,4-tetrahydroquinolin-1-yl                                   CF.sub.3 CF.sub.2 CH.sub.2                                                                  2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          CF.sub.3 CF.sub.2 CF.sub.2                                                                  piperidino                                                        CF.sub.3 CF.sub.2 CF.sub.2                                                                  2-methylpiperidino                                                CF.sub.3 CF.sub.2 CF.sub.2                                                                  indol-1-yl                                                        CF.sub.3 CF.sub.2 CF.sub.2                                                                  perhydroindol-1-yl                                                CF.sub.3 CF.sub.2 CF.sub.2                                                                  1,2,3,4-tetrahydroquinolin-1-yl                                   CF.sub.3 CF.sub.2 CF.sub.2                                                                  2-methyl-1,2,3,4-tetrahydroquinolin-1-yl                          ______________________________________                                    

If, for example, 1-(2-chloroethyl)-5(4H)-tetrazolinone and N-isopropyl-N-phenyl carbamoyl chloride are used as the starting materials, the reaction is illustrated by the following equation: ##STR9##

In process (a) according to the invention, starting compounds of the formula (II) mean compounds based on the above definition of R¹, preferably compounds based on the above preferred definitions.

The starting compounds of the formula (II) are novel, and can be obtained by the following processes:

(b) compounds of the formula:

    R.sup.1 --NCO                                              (IV)

wherein R¹ is defined as above,

are reacted with trimethylsilyl azide,

if appropriate in the presence of catalysts,

and then are reacted with portic solvents, or,

(c) compounds represented by the above formula (IV) are reacted with sodium azide, in the presence of catalysts and in the presence of inert solvents, or,

(d) compounds represented by the formula: ##STR10## wherein R¹ is defined as above, are reacted with trimethylsilyl azide, and then are reacted with portic solvents, or,

(e) compounds represented by the formula: ##STR11## wherein R¹ is as defined above, are reacted with sodium azide, in the presence of catalysts and in the presence of inert solvents, or,

(f) compounds represented by the formula: ##STR12## wherein R¹ is as defined above, are reacted with compounds represented by the formula: ##STR13## wherein R⁴ is hydrogen, methyl or ethyl, in the presence of acid binders, if appropriate in the presence of inert solvents.

In the processes (b) and (c), the compounds of formula (IV) used as starting material are known per se and specific examples thereof include the following compounds:

2-chloroethyl isocyanate, 2-bromoethyl isocyanate, 2-fluoroethyl isocyanate, 1-chloroethyl isocyanate, 1-bromoethyl isocyanate, 1,2-dichloroethyl isocyanate, 1,2-dibromoethyl isocyanate, chloromethyl isocyanate, bromomethyl isocyanate, dichloromethyl isocyanate, trichloromethyl isocyanate, trifluoromethyl isocyanate, 3-chloropropyl isocyanate, 3-bromopropyl isocyanate, 3-fluoropropyl isocyanate, 2,2,3,3,3-pentafluoropropyl isocyanate, perfluoropropyl isocyanate, and the like.

In the process (d), the compounds of formula (V) used as starting material are known per se and specific examples thereof include the following compounds:

2-chloropropionyl chloride, 2-bromopropionyl chloride, 3-chloropropionyl chloride, 3-bromopropionyl chloride, 2,3-dichloropropionyl chloride, 2,3-dibromopropionyl chloride, perfluoropropionyl chloride, 3-chlorotetra-fluoropropionyl chloride, 1,1,2,2-tetrafluoropropionyl chloride, chloroacetyl chloride, bromoacetyl chloride, dichloroacetyl chloride, trichloroacetyl chloride, trifluoroacetyl chloride, 4-chlorobutyryl chloride, 3,4-dichloropentafluorobutyryl chloride, and the like.

The compounds of above formula (V) can be easily obtained by chlorinating of the formula: ##STR14## wherein R¹ is as defined above, according to conventional method.

Compounds of formula (IX) are known per se and include the following:

2-chloropropionic acid, 2-bromopropionic acid, 3-chloro-propionic acid, 3-bromopropionic acid, 2,3-dichloro-propionic acid, 2,3-dibromopropionic acid, perfluoro-propionic acid, 3-chloro-tetrafluoropropionic acid, 1,1,2,2-tetrafluoropropionic acid, chloroacetic acid, bromoacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, 4-chlorobutyric acid, 3,4-di-chloropentafluoro butyric acid, and the like.

In the above process (e), compounds of formula (VI) are known and include following:

phenyl-N-(2-chloroethyl) carbamate, phenyl-N-(2-bromo-ethyl) carbamate, phenyl-N-(2-fluoroethyl) carbamate, phenyl-N-(2,2,2-trifluoroethyl) carbamate, phenyl-N-(2,2,3,3,3-pentafluoro-propyl) carbamate, phenyl-N-(3-chloropropyl) carbamate, and the like.

In the process (f), compounds of formula (VII) used as starting material are novel, and can be obtained compounds of the following formula: ##STR15## wherein R¹ is defined as above, and R⁵ is C₁₋₄ alkyl, are reacted with sodium azide, in the presence of inert solvents.

This reaction can be conducted, for example, by the method known per se and described in Berichte, Vol. 28, pp. 74-76, 1895.

The compounds (X) used in the above process (f) are known per se and are specifically exemplified by the following compounds:

methyl (or ethyl) {N-(2,2,2-trifluoroethyl)}dithio carbamate, methyl (or ethyl) {N-(2-chloroethyl)}dithio carbamate, methyl (or ethyl) {N-(2-bromoethyl)}dithio carbamate, methyl (or ethyl) {N-(2-fluoroethyl)} dithio carbamate, methyl (or ethyl) {N-(2,2,3,3,3-pentafluoro-propyl)} dithio carbamate, methyl (or ethyl) {N-(3-chloropropyl) }dithio carbamate, and the like.

In the process (a) according to the invention, starting compounds of the formula (III) mean compounds based on the above definition of R², R³ and hal, preferably compounds based on the above preferred definitions.

In the process (a), compounds of formula (III) used as starting material are known per se and exemplified by the following compounds:

diisopropylcarbamoyl chloride (and bromide), diethyl-carbamoyl chloride (and bromide), dimethylcarbamoyl chloride (and bromide), dipropargylcarbamoyl chloride (and bromide), diallylcarbamoyl chloride (and bromide), N-methyl-N-ethylcarbamoyl chloride (and bromide), N-methyl-N-n-propylcarbamoyl chloride (and bromide), N-methyl-N-isopropylcarbamoyl chloride (and bromide), N-methyl-N-cyclopropylcarbamoyl chloride (or bromide), N-methyl-N-sec-butylcarbamoyl chloride (and bromide), N-methyl-N-cyclopentylcarbamoyl chloride (and bromide), N-methyl-N-cyclohexylcarbamoyl chloride (and bromide), N-methyl-N-phenylcarbamoyl chloride (and bromide), N-methyl-N-1-methyl-2-propenylcarbamoyl chloride (and bromide), N-ethyl-N-n-propylcarbamoyl chloride (and bromide), N-ethyl-N-cyclopropylcarbamoyl chloride (and bromide), N-ethyl N-cyclopropylcarbamoyl chloride (and bromide), N-ethyl-N-sec-butylcarbamoyl chloride (and bromide), N-ethyl-N-cyclopentylcarbamoyl chloride (and bromide), N-ethyl-N-cyclohexylcarbamoyl chloride (and bromide), N-ethyl-N-phenylcarbamoyl chloride (and bromide), N-n-propyl-N-iso-propylcarbamoyl chloride (and bromide), N-n-propyl-N-cyclopropylcarbamoyl chloride (and bromide), N-n-propyl-N-sec-butylcarbamoyl chloride (and bromide), N-n-propyl-N-cyclopentylcarbamoyl chloride (and bromide), N-n-propyl-N-cyclohexylcarbamoyl chloride (and bromide), N-isopropyl-N-phenylcarbamoyl chloride (and bromide), N-isopropyl-N-allylcarbamoyl chloride (and bromide), 1-pyrrolidine-carbonyl chloride (and bromide), 1-piperidinecarbonyl chloride (and bromide), 4-morpholinecarbonyl chloride (and bromide), 1-(2-methyl-piperidine)carbonyl chloride (and bromide), 1-(2,5-di-methylpyrrolidine)carbonyl chloride (and bromide), 1-(2,6-dimethylpiperidine)carbonyl chloride (and bromide), 1-(2-methyl-1,2,3,4-tetrahydroquinoline)-carbonyl chloride (and bromide), 1-(perhydroindole)-carbonyl chloride (and bromide), and 1-(perhydroquinoline)-carbonyl chloride (and bromide).

As appropriate diluents for carrying out the process (a) according to the invention there may be mentioned any kind of inert solvents.

Examples of such diluents are aliphatic, alicyclic and aromatic hydrocarbons (which may optionally be chlorinated) such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, di-chloromethane, chloroform, carbon tetrachloride, 1,2-di-chloroethane, chlorobenzene and dichlorobenzene; ethers such as diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) and diethyleneglycol dimethyl ether (DGM); nitriles such as acetonitrile and propionitrile; bases such as pyridine; and others.

The process (a) is carried out usually in the presence of acid binding agents such as inorganic bases such as hydroxides, carbonates and bicarbonates of alkali metals including sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; inorganic alkali metal amides including lithium amide, sodium amide, potassium amide and the like; and organic bases such as alcoholate, tertiary amines, dialkylaminoanilines and pyridines such as triethylamine, 1,1,4,4-tetramethyl ethylenediamine (TMEDA), N,N-dimethyl-aniline, N,N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), 1,4-diazabi-cyclo 2,2,2!octane (DABCO), 1,8-diazabicyclo 5,4,0!undec-7-ene (DBU), and the like.

Further, the process (a) can be carried out in the presence of catalysts such as by 4-dimethylaminopyridine (DMAP).

In the process (a), the reaction temperature can be varied within a substantially wide range. In general, the reaction is carry out at a temperature of from about 0° C. to about 150° C., preferably about 25° C. to about 100° C.

Also, the reactions can be carried out under atmospheric pressure but may also be under an elevated or reduced pressure.

In carrying out the process (a) according to the invention, the desired compound of the formula (I) can be obtained by reacting about 1 to 1.5 moles of the compound of formula (III) in a diluent such as acetonitorile with 1 mole of the compound of formula (II) in the presence of acid binder, for example, in the presence of 1 to 1.5 moles of 4-dimethylaminopyridine.

In case of using an acid binding agent other than 4-dimethylaminopyridine in these reactions, it is usually preferable to use a catalytic amount of, e.g., 0.03 molar amount to 0.1 molar amount of 4-dimethylaminopyridine in order to selectively obtain the compound of formula (I).

In the above process (b) is usually conducted in the presence of catalysts and the catalysts useful in such cases are exemplified by boron trifluoride ethyl etherate, aluminum chloride, diethylaluminum chloride, and the like.

In the process (b), the reaction temperature can be varied within a substantially wide range. In general, the reaction is carry out at a temperature of from about 0° C. to about 200° C., preferably about 50° C. to about 150° C.

Also, the reaction can be carried out under atmospheric pressure but may also be carryed out under an elevated or reduced pressure.

In carrying out the process (b) according to the invention, the desired compound of the formula (II) can be obtained by reacting about 1 to 1.5 moles of trimethylsilyl azide with 1 mole of the compound of formula (IV) in the presence of catalyst, for example, a catalytic amount of boron trifluoride ethyl etherate.

In the prosesses (b) and (d), after reaction is completed, protic solvents are added, and the protic solvents in this case are exemplified by water, methanol, ethanol, n-propanol, isopropanol, and acetic acid, preferably, methanol.

As appropriate diluents for carrying out the process (c) according to the invention there may be mentioned any kind of inert solvents.

Examples of such diluents are exemplified by acid amides such as N,N-dimethylformamide (DMF), N,N-dimethylaceto-amide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, hexamethyl phosphoric triamide (HMPA); sulfone, sulfoxides such as dimethylsulfoxide (DMSO), sulfolane, and the like.

In the process (c) is usually carried out in the presence of catalysts, exemplified by aluminum chloride, boron trichloride, diethylaluminum chloride, and the like.

In the process (c), the reaction temperature can be varied within a substantially wide range. In general, the reaction is carry out at a temperature of from about 0° C. to about 200° C., preferably about 20° C. to about 150° C.

The reactions can be carried out under atmospheric pressure but may also be carryed out under an elevated or reduced pressure.

In carrying out the process (c) according to the invention, the desired compound of the formula (II) can be obtained by reacting about 1 to 1.5 moles of sodium azide with 1 mole of the compound of formula (IV) in the presence of catalyst, for example, 0.01 to 1 mole of aluminum chloride.

In the process (d), the reaction temperature can be varied within a substantially wide range. In general, the reaction is carry out at a temperature of from about 0° C. to about 200° C., preferably about 25° C. to about 130° C.

The reactions can be carried out under atmospheric pressure but may also be carryed out under an elevated or reduced pressure.

In carrying out the process (d) according to the invention, the desired compound of the formula (II) can be obtained by reacting about 2.5 to 4 moles of trimethylsilyl azide with 1 mole of the compound of formula (V).

As appropriate diluents for carrying out the process (e) according to the invention there may be mentioned any kind of inert solvents.

Examples of such diluents are water; acid amides such as dimethylformamide (DMF), dimethyl acetoamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, hexamethyl phosphoric triamide (HMPA); sulphoxides such as dimethyl sulfoxide (DMSO), sulfolane, and the like.

In the above process (e) is carried out preferably in the presence of catalysts and the catalyst is exemplified by aluminum chloride.

In the above-mentioned process (e), the reaction temperature can be varied within a substantially wide range. In general, the reaction is carried out at a temperature of from about -30° C. and about 50° C., preferably from 0° C. to 30° C.

The reactions can be carried out under atmospheric pressure but may also be optionally operated under an elevated or reduced pressure.

In carrying out the process (e) according to the invention, the desired compound of the formula (II) can be obtained by reacting about 1 to 1.3 moles of sodium azide in a diluent with 1 mole of the compound of formula (V)in the presence of 1 to 1.2 moles of aluminum chloride.

As appropriate diluents for carrying out the process (f) according to the invention there may be mentioned any kind of inert solvents.

Examples of such diluents are water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene-glycol, and others.

The above mentioned process (f) is carried out preferably in the presence of acid binding agents, and as examples of such acid binding agents there may be mentioned inorganic bases including hydroxides, carbonates and bicarbonates of alkali metals such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and the like.

In the above-mentioned process (f), the reaction temperature can be varied within a substantially wide range. In general, the reaction is carried out at a temperature of from about -30° C. and about 50° C., preferably from 0° C. to 30° C.

The reactions can be carried out under atmospheric pressure but may also be carryed out under an elevated or reduced pressure.

In carrying out the process (f) according to the invention, the desired compound of the formula (II) can be obtained by reacting about 1 to 1.3 moles of the compound of formula (VIII) in a diluent with 1 mole of the compound of formula (VII)in the presence of 1 to 1.2 moles of acid binding agent.

The tetrazolinone derivatives according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weedkillers.

By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The tetrazolinone derivatives according to the invention can be used, for example, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver and Centaurea.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the tetrazolinone derivatives according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The tetrazolinone derivatives according to the invention are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the tetrazolinone derivatives according to the invention can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, and for the selective combating of weeds in annual cultures.

The tetrazolinone derivatives according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, foams, pastes, granules, tablets, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances, coating compositions for use on seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans and fumigating coils, as well as ULV cold mist and warm mist formulations.

These formulations may be produced in known manner, for example by mixing the tetrazolinone derivatives according to the invention with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents.

As liquid solvents diluents or carriers, there are suitable in the main, aromatic hydrocarbons, such as xylene, toluene or alkyl napthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl-isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethyl-sulphoxide.

By liquefied gaseous diluents or carriers are meant liquids which would be gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.

As solid carriers there may be used ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates. As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.

As emulsifying and/or foam-forming agents there may be used non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products.

Dispersing agents include, for example, lignin sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulation.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dye stuffs, azo dye stuffs or metal phthalocyanine dye stuffs, and trace nutrients, such as salts of iron, manganese boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain from 0.1 to 95 per cent by weight of tetrazolinone derivatives according to the invention, preferably from 0.5 to 90 per cent by weight.

The tetrazolinone derivatives according to the invention, as such or in the form of their formulations, can also be used, for combating weeds, as mixtures with known herbicides, finished formulations or tank mixes being possible.

Mixtures with other known active compounds, such as herbicides, fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.

The tetrazolinone derivatives according to the invention can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

The tetrazolinone derivatives according to the invention can be applied either before or after emergence of the plants.

They can also be incorporated into the soil before sowing. They are used, in particular, after emergence of the plants.

The amount of tetrazolinone derivatives according to the incention used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.001 and 10 kg of tetrazolinone derivatives according to the invention per hectare of soil surface, preferably between 0.01 and 5 kg per ha.

EXAMPLES

The preparation and use of the tetrazolinone derivatives according to the invention can be seen from the following examples.

Synthesis Example 1 ##STR16##

1-(2-Chloroethyl)-5(4H)-tetrazolinone (2 g), DMAP (1.97 g) and N-isopropyl-N-phenyl-carbamoyl chloride (3.17 g) were dissolved in acetonitrile (30 ml), then reacted for 6 hours by heating with refluxing. After distilling off the solvent under reduced pressure, chloroform (30 ml) was added to the residue and was washed with water (20 ml×2). The chloroform layer was dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to flash column chromatography (hexane:ethyl acetate=5:2) to give 1-(2-chloroethyl)-4-(N-isopropyl-N-phenyl carbamoyl)-5(4H)-tetrazolinone (3.22 g). _(D) ²⁰ 1.5329

Synthesis Example 2 ##STR17##

1-(2-Chloroethyl)-5(4H)-tetrazolinone (2 g), DMAP (82 mg), potassium carbonate (2.23 g) and N-isopropyl-N-phenyl-carbamoyl chloride (9.17 g) were suspended in toluene (40 ml) and heated for 17 hours at 60°-65° C. This material was washed with water (20 ml×2) and dried over anhydrous sodium sulfate, followed by distillation off of the solvent and the residue was subjected to flash column chromatography (hexane:ethyl acetate=5:2) giving 1-(2-chloroethyl)-4-N-isopropyl-N-phenylcarbamoyl)-5(4H)-tetrazolinone (3.9 g). _(D) ²⁰ 1.5329

The tetrazolinone derivatives synthesized by foregoing Synthesis Example 1 or Synthesis Example 2 are shown in Table 3 and 4 together with other compounds producible by those processes:

                  TABLE 3                                                          ______________________________________                                          ##STR18##                                                                     Com-                                                                           pound                              Physical                                    No.   R.sup.1    R.sup.2  R.sup.3  constant                                    ______________________________________                                          1    ClCH.sub.2 CH.sub.2                                                                       ethyl    ethyl    n.sub.D.sup.20 1.5013                        2    ClCH.sub.2 CH.sub.2                                                                       ethyl    cyclohexyl                                                                              n.sub.D.sup.20 1.5063                        3    ClCH.sub.2 CH.sub.2                                                                       n-propyl n-propyl n.sub.D.sup.20 1.4929                        4    ClCH.sub.2 CH.sub.2                                                                       allyl    allyl    n.sub.D.sup.20 1.5152                        5    ClCH.sub.2 CH.sub.2                                                                       propargyl                                                                               propargyl                                                                               n.sub.D.sup.20 1.5255                        6    ClCH.sub.2 CH.sub.2                                                                       methyl   phenyl   n.sub.D.sup.20 1.5517                        7    ClCH.sub.2 CH.sub.2                                                                       ethyl    phenyl   mp 78-79° C.                          8    ClCH.sub.2 CH.sub.2                                                                       n-propyl phenyl   mp 56-58° C.                          9    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               phenyl   n.sub.D.sup.20 1.5329                       10    ClCH.sub.2 CH.sub.2                                                                       n-butyl  phenyl   mp 61.5-63° C.                       11    ClCH.sub.2 CH.sub.2                                                                       phenyl   phenyl   mp 118-119° C.                       12    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               2-fluorophenyl                                                                          n.sub.D.sup.20 1.5293                       13    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               3-fluorophenyl                                                                          n.sub.D.sup.20 1.5239                       14    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               4-fluorophenyl                                                                          n.sub.D.sup.20 1.5221                       15    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               2-methylphenyl                                                                          n.sub.D.sup.20 1.5293                       16    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               3-methylphenyl                                                                          n.sub.D.sup.20 1.5287                       17    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               4-methylphenyl                                                                          mp 46.5-58° C.                       18    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               2-methylthio-                                                                           n.sub.D.sup.20 1.5523                                                 phenyl                                               19    CF.sub.3 CH.sub.2                                                                         ethyl    cyclohexyl                                                                              n.sub.D.sup.20 1.4670                       20    CF.sub.3 CH.sub.2                                                                         isopropyl                                                                               phenyl   mp 117-118° C.                       21    ClCH.sub.2 CH.sub.2 CH.sub.2                                                              isopropyl                                                                               phenyl   n.sub.D.sup.20 1.5315                       22    ClCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               2-methoxy-                                                                              mp 104.5-                                                             phenyl   106° C.                              23    BrCH.sub.2 CH.sub.2                                                                       isopropyl                                                                               phenyl   n.sub.D.sup.20 1.5418                       24    CH.sub.3 CHCl                                                                             isopropyl                                                                               phenyl   n.sub.D.sup.20 1.5335                       25    CF3CH2     isopropyl                                                                               3-methylphenyl                                                                          mp 99-101° C.                        26    CF3CH2     isopropyl                                                                               4-chlorophenyl                                                                          mp 62.5-65° C.                       27    CF.sub.3 CH.sub.2                                                                         isopropyl                                                                               3-chlorophenyl                                                                          mp 83.5-86° C.                       28    CF.sub.3 CH.sub.2                                                                         isopropyl                                                                               4-methylphenyl                                                                          mp 69.5-71° C.                       29    CF.sub.3 CH.sub.2                                                                         isopropyl                                                                               4-fluorophenyl                                                                          mp 88.5-90° C.                       30    ClCH.sub.2 CHCl                                                                           isopropyl                                                                               phenyl   n.sub.D.sup.20 1.5374                       ______________________________________                                    

                                      TABLE 4                                      __________________________________________________________________________     (in the case where R.sup.2 and R.sup.3 form a heterocyclic ring                together with the nitrogen atom to which are they are                          bonded)                                                                        Compound                      Physical                                         No.                           constant                                         __________________________________________________________________________     31                                                                                    ##STR19##              n.sub.D.sup.20 1.5654                            __________________________________________________________________________

Synthesis of Intermediate Synthesis Example 3 ##STR20##

2-chloroethyl isocyanate (10 g), trimethylsilyl azide (16.35 g) and a catalytic amount of boron trifluoride ethyl etherate were mixed and heated for 16 hours with refluxing. The excess trimethylsilyl azide was distilled off under reduced pressure and methanol was added to the residue. Thereafter, methanol was distilled off and the residue was subjected to flash column chromatography (hexane:ethyl acetate=1:1) to give 1(2-chloro-ethyl)-5(4H)-tetrazolinone (11.47 g). mp 79.5°-81.5° C.

Using 3-chloropropyl isocyanate (5 g) instead of 2-chloroethyl isocyanate in Synthesis Example 3, 1-(3-chloropropyl)-5(4H)-tetrazolinone (3.15 g) was obtained. mp 48.5°-53.5° C.

Using chloromethyl isocyanate (5 g) instead of 2-chloro-ethyl isocyanate in Synthesis Example 3, l-(chloro-methyl)-5(4H)-tetrazolinone (2.32 g) was obtained. _(D) ²⁰ 1.5091

Synthesis Example 4 ##STR21##

Anhydrous aluminum chloride (0.2 g) was added to a suspension of sodium azide (1.95 g) in anhydrous DMF (18 ml) in an argon stream under ice-cooling and stirred for 15 minutes. Then, 2-chloroethyl isocyanate (3.16 g) was dropped therein and stirring was further continued at 70°-75° C. for 3 hours in an argon stream. After cooling, the reaction mixture was poured into a mixture of sodium nitrite (0.5 g), water (100 ml) and ice (50 g) with stirring and acidified with 10% hydrochloric acid (for coloring of KI-starch paper) and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate. Then, the solvent was distilled off under a reduced pressure and the residue was subjected to flash column chromatography (hexane:ethyl acetate=1:1) to give 1-(2-chloroethyl)-5(4H)-tetrazolinone (3.61 g). mp 79.5°-81.5° C.

Synthesis Example 5 ##STR22##

2-Chloropropionyl chloride (2 g) and trimethylsilyl azide (6.9 g) were mixed and heated for 16 hours with refluxing. The excess trimethylsilyl azide was distilled off under reduced pressure and methanol was added to the residue. Thereafter, methanol was distilled off and the residue was subjected to flash column chromatography (hexane:ethyl acetate=1:1) to give 1-(1-chloroethyl)-5(4H)-tetrazolinone (1.07 g). _(D) ²⁰ 1.5058

Using 3-bromopropionyl chloride (3.43 g) instead of 2-chloropropionyl chloride (2 g), 1-(2-bromoethyl)-5(4H)-tetrazolinone (3.45 g) was obtained by the similar to that in Synthesis Example 5. mp 69.5°-73.5° C.

Using 2,3-dichloropropionyl chloride (3.23 g) instead of 2-chloropropionyl chloride (2 g), 1-(1,2-dichloroethyl)-5(4H)-tetrazolinone (1.1 g) was obtained by the process similar to that in Synthesis Example 5. _(D) ²⁰ 1.5058

Synthesis Example 6 ##STR23##

Sodium hydroxide (93%, 2.15 g) was dissolved in 10 ml of water and 1-(2,2,2-trifluoroethyl)-5-mercaptotetrazole (8.29 g) was added thereto to give a homogeneous solution. This solution was diluted with ethanol (60 ml). After cooling to 0° C., propylene oxide (3.40 g) was added dropwise while maintaining the temperature. After stirring at 0° C. for 30 minutes and then at room temperature for 2 hours, the solvent was distilled off under reduced pressure. Water (80 ml) was added to the residue and the insoluble oily matter was removed by washing with ethyl acetate. The aqueous layer was separated and acidified by hydrochloric acid followed by evaporation to dryness under reduced pressure. The residue was extracted with warm ethyl acetate and filtered. The solvent was evaporated under reduced pressure to give 1-(2,2,2-trifluoroethyl)-5(4H)-tetrazolinone (6.58 g). mp 98°-100° C.

Synthesis Example 7 ##STR24##

Methyl {N-(2,2,2-trifluoroethyl)}dithio carbamate (11.65 g) and sodium azide (4.95 g) were suspended in 80 ml of water and heated for 30 minutes with refluxing. After cooling, the reaction solution was washed with ethyl acetate and acidified with 10% hydrochloric acid for precipitation. After separation by filtration, the precipitation was dried under a reduced pressure to give 1-(2,2,2-trifluoroethyl)-5-mercapto-tetrazole (10.32 g). mp 122°-124° C.

Biological Test Examples

Test Example 1

Test of pre-emergence soil treatment test

Preparing method

carrier: acetone 5 parts by weight

emulsifier: benzyloxy polyglycol ether 1 part by weight

One part by weight of the active compound and the above amounts of a carrier and an emulsifier are mixed to give an emulsion. A prescribed amount of this emulsion is diluted with water to be subjected to the undermentioned tests.

Testing method

In the greenhouse, seeds of Echinochloa and Amaranthus lividus were sowed in the surface layer of plowed land soil filled in a 120 cm² pot with soil-covering and a prescribed amount of the above tested chemical was uniformly sprayed on the surface layer of soil in the testing pot.

The herbicidal effect was examined after 4 weeks from application.

The herbicidal effect was rated as 100% in the case of complete death and as 0% in the case where equivalent growth was observed to the case without treatment.

Result

The tetrazolinone derivatives of Compounds Nos. 1, 2, 3, 4, 7, 8, 9, 12, 13, 14, 15, 16, 17, 19, 20, 21, 24, and 25 exhibited 100% herbicidal effect against Echinochloa and Amaranthus lividus by application of 1 kg/ha of the amount.

Test Example 2

Test of post-emergency foliage treatment

Testing method

In the greenhouse, seeds of Echinochloa and Amaranthus lividus were sowed each in a 120 cm² pot filled with plowed land soil and covered with soil. After 10 days from sowing and soil-covering (when the weeds on average were in two-leaf stage), a prescribed amount of the chemical prepared similarly to those in above Test Example 1 was uniformly spread on the foliage part of each test plant in the testing pot. After 3 weeks from spreading, the herbicidal effect was examined.

Result

In this test, the tetrazolinone derivatives of Compounds Nos. 1, 2, 3, 4, 7, 8, 9, 13, 14 and 20 exhibited a herbcidal effect of 90% or more against Echinochloa and 80% or more against Amaranthus lividus by application of 2.0 kg/ha of the amount.

Formulation Example 1 (granules)

Water (25 parts) is added to a mixture of Compound No. 3 (10 parts), bentonite (montmorillonite) (30 parts), talc (58 parts) and lignin sulphonate salt (2 parts) with kneading and formed into 10-40 mesh granules using an extrusion-type granulator followed by drying at 40°-50° C.

Formulation Example 2 (granules)

A clay mineral (95 parts) having a particle size distribution of 0.2-2 mm is introduced in a rotary mixer and Compound No. 8 is sprayed therein with a liquid diluent under rotation to wet uniformly, followed by drying at 40°-50° C.

Formulation Example 3 (emulsion)

An emulsion is obtained by mixing Compound No. 20 (30 parts), xylene (5 parts), polyoxyethylene alkyl phenyl ether (8 parts) and calcium alkylbenzene sulphonate (7 parts) with stirring.

Formulation Example 4 (wettable powder)

A wettable powder is prepared by mixing Compound No. 1 (15 parts), a mixture (1:1) of White Carbon (fine powder of hydrated non-crystalline silicon oxide) (80 parts) and powdery clay, sodium alkylbenzene sulphonate (2 parts) and a condensate of sodium alkylnaphthalene sulphonate and formaldehyde (3 parts) in a powdery state.

Formulation Example 5 (wettable granules)

Wettable granules are prepared by thoroughly mixing Compound No. 2 (20 parts), sodium lignin sulphonate (30 parts), bentonite (15 parts) and calcined diatomaceous earth powder (35 parts) followed by addition of water and extrusion through a 0.3 mm screen and drying.

It will be understood that the specification and examples are illustrative but not limitative to the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skill in the art. 

We claim:
 1. A tetrazolinone derivative of the formula: ##STR25## wherein R¹ is alkyl substituted by halogen, andR² and R³ each independently is alkyl, alkenyl, alkynyl, cycloalkyl which may optionally be substituted, phenyl or substituted phenyl, or R² and R³ together with the N-atom to which they are attached, are a 5- or 6-membered heterocyclic ring which may optionally be substituted.
 2. A tetrazolinone derivative according to claim 1, whereinR¹ is C₁₋₆ alkyl which is substituted by one or more of fluorine, chlorine or bromine, and R² and R³ each independently is C₁₋₆ alkyl, C₂₋₆ alkenyl, C₃₋₆ alkynyl, c₃₋₈ cycloalkyl which may optionally be substituted by C₁₋₆ alkyl, or phenyl or phenyl having at least one substituent selected from the group consisting of halogen, cyano, nitro, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio and C₁₋₄ haloalkylthio, or R² and R³ together with the N-atom to which they are attached, are a 5- or 6-membered saturated heterocyclic ring optionally substituted by alkyl and/or condensed with a hydrocarbon ring.
 3. A tetrazolinone derivative according to claim 1, whereinR¹ is C₁₋₃ alkyl which is substituted by one or more of fluorine, chlorine or bromine, and R² and R³ each independently is C₁₋₄ alkyl, cyclopropyl which may optionally be substituted by methyl, cyclopentyl which may optionally be substituted by methyl, cyclohexyl which may optionally be substituted by methyl, allyl, propargyl, phenyl, or phenyl having at least one substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, methylthio, nitro, cyano, trifluoromethyl, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, trifluoromethylthio and 2,2,2-trifluoroethylthio, or R² and R³ together with the N-atom to which they are attached, are piperidino, methylpiperidino, morpholino, indol-1-yl, perhydroindol-1-yl, 1,2,3,4-tetrahydroquinolin-1-yl, 2-methyl-1,2,3,4-tetrahydro-quinolin-1-yl, or perhydroquinolin-1-yl.
 4. A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1 and a diluent.
 5. A method of combating unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidal effective amount of a compound according to claim
 1. 6. A compound of the formula: ##STR26## wherein R¹ is alkyl substituted by halogen.
 7. A compound according to claim 6, in whichR¹ is C₁₋₆ alkyl which is substituted by one or more of fluorine, chlorine or bromine.
 8. A compound according to claim 6, in whichR¹ is C₁₋₃ alkyl which is substituted by one or more of fluorine, chlorine or bromine.
 9. A tetrazolinone derivative of the formula: ##STR27## wherein R¹ is C₁₋₆ -alkyl which is substituted by one or more of fluorine, chlorine or bromine; andR² and R³ each independently is C₁₋₆ -alkyl, C₂₋₆ -alkenyl, C₃₋₆ -alkynyl, C₃₋₈ -cycloalkyl which may optionally be substituted by C₁₋₆ -alkyl, or phenyl or phenyl having at least one substituent selected from the group consisting of halogen, cyano, nitro, C₁₋₄ -alkyl, C₁₋₄ -haloalkyl, C₁₋₄ -alkoxy, C₁₋₄ -haloalkoxy, C₁₋₄ -alkylthio and C₁₋₄ -haloalkylthio; or R² and R³ together with the N-atom to which they are bonded, form piperidino, methylpiperidino, morpholino, indol-1-yl, perhydroindol-1-yl, 1,2,3,4-tetrahydroquinolin-1-yl, 2-methyl-1,2,3,4-tetrahydroquinolin1yl, or perhydroquinolin-1-yl.
 10. A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 9 and a diluent.
 11. A method of combating unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound according to claim
 9. 